Acetic Acid → HCID 68959411, compound

HRID 1725625Notes

Reaction equation

HRID 1725625 reaction equation
N[CH2:2][CH:3]([S:10][CH2:11][C@H:12]([C:21]([O:23][CH3:24])=[O:22])[NH:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[C:25](O)(=O)[CH3:26].[C:29]([BH3-])#[N:30].[Na+].[C:33](=O)(O)[O-].[Na+]>CO>[C:17]([O:16][C:14]([NH:13][C@@H:12]([C:21]([O:23][CH3:24])=[O:22])[CH2:11][S:10][CH:3]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[CH2:2][NH:30][CH2:29][CH:26]1[CH2:25][CH2:33]1)=[O:15])([CH3:20])([CH3:19])[CH3:18]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 516892Sodium BicarbonateHCID 5003444Sodium cyanoborohydrideHCID 57562519HCID 57562519, compound

Product 1

HCID 68959411HCID 68959411, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Cyclopropanecarboxaldheyde (104 mg, 1.48 mmol) was added to a solution of methyl S-(2-amino-1-phenylethyl)-N-(tert-butoxycarbonyl)-D-cysteinate (583 mg, 1.65 mmol) in methanol (25 mL) adjusted to pH 6 with acetic acid. After 15 min, sodium cyanoborohydride (155 mg, 2.47 mmol) was added. After an additional 1 h, saturated aqueous sodium bicarbonate was added and the mixture was extracted with dichlormethane (2×). The combined organic extracts were dried over magnesium sulfate, filtered, and concentrated. Purification by silica gel [100% dichloromethane->97% dichloromethane/3% (10% ammonium hydroxide in methanol)] gave the title compound (305 mg). MS 409 (M+1).

Workup

  1. waitAfter an additional 1 h
  2. extractionthe mixture was extracted with dichlormethane (2×)
  3. dry with materialThe combined organic extracts were dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification by silica gel [100% dichloromethane->97% dichloromethane/3% (10% ammonium hydroxide in methanol)]

Sources & evidence

ORD record
ord-5de0ddbdea624aa8928b2d7de1e1d97b
Source dataset
uspto-grants-2009_02
Patent number
US07491713B2

Reaction notes

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