Acetic Acid → HCID 68461424, compound

HRID 507430Notes

Reaction equation

HRID 507430 reaction equation
[CH2:1]([O:8][C:9](=[O:22])[CH:10]([NH:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:11][CH:12]=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC(O)=O.C(O[Na])(C)=O.[NH2:32][C@H:33]([C:36]([O:38][CH3:39])=[O:37])[CH2:34][SH:35].Cl>C(O)C.O>[CH3:39][O:38][C:36]([CH:33]1[CH2:34][S:35][CH:12]([CH2:11][CH:10]([C:9]([O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[O:22])[NH:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[NH:32]1)=[O:37]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 2733208L-Cysteine, methyl ester, hydrochlorideHCID 143577952-Tert-butoxycarbonylamino-4-oxo-butyric acid benzyl esterHCID 178418247HCID 178418247, compound

Product 1

HCID 68461424HCID 68461424, compoundYield 83.8%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

To a solution of 2 (0.7 g, 2.25 mmol), AcOH (0.14 g, 2.25 mmol), AcONa (0.38 g, 4.50 mmol) in ethanol and water (10:1, 11 mL) was added L-Cys-OMe.HCl (0.39 g, 2.25 mmol). After being stirred overnight, the mixture was poured into 100 mL water, extracted with ethyl acetate, and the organic phase was dried and concentrated to give an oily crude product (0.8 g, 82%), which was used directly in the next step. 1H NMR (400 MHz, CDCl3) δ1.43 (s, 9 H), 1.95-2.15 (m, 2 H), 2.29-2.41 (m, 1H), 2.87 (m, 1 H), 3.68 (m, 1 H), 3.77 (s, 3 H), 3.96 (m, 0.6 H), 4.50 (m, 1 H), 4.70 (m, 0.4 H), 5.12-5.23 (m, 2 H), 5.35 (d, 0.4 H), 5.75 (d, 0.6 H), 7.36 (m, 5H).

Workup

  1. extractionextracted with ethyl acetate
  2. customthe organic phase was dried
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-b3952440ab35435396e4f0c999f5eb82
Source dataset
uspto-grants-2010_08
Patent number
US07786163B2

Reaction notes

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