Diisopropylethylamine → HCID 90060340, compound

HRID 1779219Notes

Reaction equation

HRID 1779219 reaction equation
[C:1]([Si:5]([CH3:43])([CH3:42])[O:6][CH2:7][CH2:8][C@:9]([OH:41])([C@H:17](/[CH:21]=[CH:22]/[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][C:29]1([CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH3:40])[O:33][CH2:32][CH2:31][O:30]1)[C:18]([O-])=[O:19])[C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])([CH3:4])([CH3:3])[CH3:2].Cl.[NH2:45][C@@H:46]([CH2:52][C:53]1[CH:58]=[CH:57][C:56]([O:59][CH:60]([CH2:62][CH3:63])C)=[CH:55][CH:54]=1)[C:47]([O:49][CH2:50][CH3:51])=[O:48].[CH:64](N(CC)C(C)C)(C)C.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1>CN(C)C=O>[C:1]([Si:5]([CH3:43])([CH3:42])[O:6][CH2:7][CH2:8][C@:9]([OH:41])([C@@H:17]([C:18](=[O:19])[NH:45][C@H:46]([C:47]([O:49][CH2:50][CH3:51])=[O:48])[CH2:52][C:53]1[CH:54]=[CH:55][C:56]([O:59][CH2:60][C:62]#[C:63][CH3:64])=[CH:57][CH:58]=1)/[CH:21]=[CH:22]/[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][C:29]1([CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH3:40])[O:33][CH2:32][CH2:31][O:30]1)[C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 131734866HCID 131734866, compoundHCID 131734867HCID 131734867, compound

Product 1

HCID 90060340HCID 90060340, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

No. 5328627, 1-tert-butyl (2S,3S)-2-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-3-[(E)-8-(2-heptyl-[1,3]dioxolan-2-yl)-oct-1-enyl]-2-hydroxy-succinate (2.81 g, 4.47 mmol) was dissolved in N,N-dimethylformamide (70 mL) and the mixture was then cooled to 0° C. in an ice bath. No. 5328632 (ethyl (S)-2-amino-3-(4-but-2-yloxy-phenyl)-propionate hydrochloride; 1.46 g, 4.90 mmol), N,N-diisopropylethylamine (3.1 mL, 17.80 mmol), and O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (1.87 g, 4.92 mmol) were added in this order, and the mixture was then stirred at 0° C. for 1.5 hours. After quenching with a mixture of a cooled solution (14 mL) of 0.5 M potassium hydrogen sulfate and water (84 mL), the mixture was extracted with 20% ethyl acetate/n-hexane (54 mL). The aqueous layer was further extracted three times with 20% ethyl acetate/n-hexane (27 mL). The organic layers were combined, and then washed with a mixture of a saturated aqueous solution (2.8 mL) of sodium chloride and water (14 mL), and with a saturated aqueous solution (14 mL) of sodium chloride in this order. The organic layers were combined, and then dried over anhydrous sodium sulfate. After filtration, the solvent was distilled off under reduced pressure to obtain 3.95 g (4.53 mmol, quant.) of tert-butyl (E)-(2S,3S)-2-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-3-[(S)-2-(4-but-2-ynyloxy-phenyl)-1-ethoxycarbonyl-ethylcarbamoyl]-11-(2-heptyl-[1,3]dioxolan-2-yl)-2-hydroxy-undec-4-enoate.

Workup

  1. customAfter quenching with a mixture of a cooled solution (14 mL) of 0.5 M potassium hydrogen sulfate and water (84 mL)
  2. extractionthe mixture was extracted with 20% ethyl acetate/n-hexane (54 mL)
  3. extractionThe aqueous layer was further extracted three times with 20% ethyl acetate/n-hexane (27 mL)
  4. washwashed with a mixture of a saturated aqueous solution (2.8 mL) of sodium chloride and water (14 mL)
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationAfter filtration
  7. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-1a41b430ff9648379294638265e6049d
Source dataset
uspto-grants-2016_02
Patent number
US09266853B2

Reaction notes

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