Water → HCID 131734843, compound

HRID 1779157Notes

Reaction equation

HRID 1779157 reaction equation
[C:1]([Si:5]([CH3:60])([CH3:59])[O:6][CH2:7][CH2:8][C@:9]([OH:58])([C@@H:17]([C:38](=[O:57])[NH:39][C@H:40]([C:53]([O:55]C)=[O:54])[CH2:41][C:42]1[CH:47]=[CH:46][C:45]([O:48][CH2:49][C:50]#[C:51][CH3:52])=[CH:44][CH:43]=1)/[CH:18]=[CH:19]/[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][C:26]1([CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37])[O:30][CH2:29][CH2:28][O:27]1)[C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])([CH3:4])([CH3:3])[CH3:2].O.C(N(CC)CC)C.[Br-].[Li+]>C(#N)C>[C:1]([Si:5]([CH3:59])([CH3:60])[O:6][CH2:7][CH2:8][C@:9]([OH:58])([C@@H:17]([C:38](=[O:57])[NH:39][C@H:40]([C:53]([OH:55])=[O:54])[CH2:41][C:42]1[CH:47]=[CH:46][C:45]([O:48][CH2:49][C:50]#[C:51][CH3:52])=[CH:44][CH:43]=1)/[CH:18]=[CH:19]/[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][C:26]1([CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37])[O:30][CH2:29][CH2:28][O:27]1)[C:10]([O:12][C:13]([CH3:14])([CH3:16])[CH3:15])=[O:11])([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 82050Lithium BromideHCID 123758623HCID 123758623, compound

Product 1

HCID 131734843HCID 131734843, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
50 °C

Procedure

No. 5327507 (Compound C; 1.09 g, 1.27 mmol) was dissolved in acetonitrile (10.9 mL), and then water (0.109 mL), triethylamine (1.06 mL, 7.61 mmol), and lithium bromide (2.91 g, 33.5 mmol) were added at room temperature. The reaction solution was stirred at 50° C. for 3.5 hours, then cooled to room temperature, quenched by the addition of 1 M hydrochloric acid (30 mL), and then extracted with ethyl acetate (100 mL). The organic layer was washed twice with water (100 mL) and then with a saturated aqueous solution of sodium chloride (100 mL). The organic layer was dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure to obtain 1.08 g (purity 71%, ESI (LC/MS positive mode) m/z 845 (M+H); Rt 3.32 min.) of Compound I, tert-butyl (E)-(2S,3S)-2-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-3-[(S)-2-(4-but-2-ynyloxy-phenyl)-1-carboxy-ethylcarbamoyl]-11-(2-heptyl-[1,3]dioxolan-2-yl)-2-hydroxy-undec-4-enoate as a crude product.

Workup

  1. temperaturecooled to room temperature
  2. customquenched by the addition of 1 M hydrochloric acid (30 mL)
  3. extractionextracted with ethyl acetate (100 mL)
  4. washThe organic layer was washed twice with water (100 mL)
  5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-4b020f5d3c404f70b2845d1b470e91a3
Source dataset
uspto-grants-2016_02
Patent number
US09266853B2

Reaction notes

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