Diisopropylethylamine → HCID 86573863, compound

HRID 2278380Notes

Reaction equation

HRID 2278380 reaction equation
Cl.[NH2:2][CH2:3][C:4]1[S:8][C:7]([C@H:9]([N:12]([CH2:25][CH:26]([CH3:28])[CH3:27])[S:13]([C:16]2[CH:24]=[CH:23][C:19]3[N:20]=[CH:21][S:22][C:18]=3[CH:17]=2)(=[O:15])=[O:14])[CH2:10][OH:11])=[CH:6][CH:5]=1.[CH3:29][O:30][C:31]([NH:33][C@H:34]([C:48](O)=[O:49])[CH:35]([C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1)[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)=[O:32].CCN(C(C)C)C(C)C.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1>CN(C=O)C>[S:22]1[C:18]2[CH:17]=[C:16]([S:13]([N:12]([CH2:25][CH:26]([CH3:28])[CH3:27])[C@@H:9]([C:7]3[S:8][C:4]([CH2:3][NH:2][C:48](=[O:49])[C@H:34]([CH:35]([C:36]4[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=4)[C:42]4[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=4)[NH:33][C:31]([O:30][CH3:29])=[O:32])=[CH:5][CH:6]=3)[CH2:10][OH:11])(=[O:15])=[O:14])[CH:24]=[CH:23][C:19]=2[N:20]=[CH:21]1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 10017620(S)-2-methoxycarbonylamino-3,3-diphenyl-propionic acidHCID 117629145HCID 117629145, compound

Product 1

HCID 86573863HCID 86573863, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of N-{(1R)-1-[5-(aminomethyl)thiophen-2-yl]-2-hydroxyethyl}-N-(2-methylpropyl)-1,3-benzothiazole-6-sulfonamide hydrochloride (30 mg, 0.065 mmol), N-(methoxycarbonyl)-β-phenyl-L-phenylalanine (21 mg, 0.071 mmol) and DIPEA (45 μL, 0.26 mmol) in DMF (300 μL) at 0° C. was added BOP (32 mg, 0.071 mmol). The reaction mixture was stirred at 0° C. for 4 hours before being quenched with a saturated solution of sodium bicarbonate (3 mL). The quenched mixture was extracted with ether/ethyl acetate (1/1 3×3 mL). The organic layers were combined and washed with brine, dried over magnesium sulfate, filtered and concentrated under reduced pressure. The crude was purified on silica gel eluting with hexanes and ethyl acetate. MS: m/z=729.1 (MNa+).

Workup

  1. custombefore being quenched with a saturated solution of sodium bicarbonate (3 mL)
  2. extractionThe quenched mixture was extracted with ether/ethyl acetate (1/1 3×3 mL)
  3. washwashed with brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe crude was purified on silica gel eluting with hexanes and ethyl acetate

Sources & evidence

ORD record
ord-dc8f381a7dc745a795f072a87370e669
Source dataset
uspto-grants-2015_09
Patent number
US09133157B2

Reaction notes

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