Sodium Methoxide → (S)-benzyl 4-mercapto-1-oxo-1-(5-oxopentylamino)butan-2-ylcarbamate

HRID 529497Notes

Reaction equation

C(=O)([S:3][CH2:4][CH2:5][C@H:6]([NH:16][C:17]([O:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:18])[C:7](=[O:15])[NH:8][CH2:9][CH2:10][CH2:11][CH2:12][CH:13]=[O:14])C.C[O-].[Na+]>CO>[SH:3][CH2:4][CH2:5][C@H:6]([NH:16][C:17](=[O:18])[O:19][CH2:20][C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)[C:7](=[O:15])[NH:8][CH2:9][CH2:10][CH2:11][CH2:12][CH:13]=[O:14]

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of (S)—S-3-(benzyloxycarbonylamino)-4-oxo-4-(5-oxopentylamino)butyl ethanethioate (195 mg, 0.494 mmol) in methanol (4 mL) was purged with argon for 10 min and then cooled to 0° C. Sodium methoxide in MeOH (25%, 0.12 mL) was added to the reaction. The mixture was stirred at 0° C. for 10 min. The reaction was quenched with saturated aqueous NH4Cl solution. The reaction was extracted with EtOAc (2×). The combined EtOAc extracts were washed with saturated aqueous NH4Cl solution, water, saturated aqueous NaCl, dried over Na2SO4, filtered and concentrated. The white solid residue was dried under vacuum to give (S)-benzyl 4-mercapto-1-oxo-1-(5-oxopentylamino)butan-2-ylcarbamate (150 mg, 0.426 mmol, 86% yield) as a white solid. Anal. Calcd. for C12H24N2O4S m/z 352.4. found: 353.23 (M+H)+.

Workup

customThe reaction was quenched with saturated aqueous NH4Cl solution
extractionThe reaction was extracted with EtOAc (2×)
washThe combined EtOAc extracts were washed with saturated aqueous NH4Cl solution, water, saturated aqueous NaCl
dry with materialdried over Na2SO4
filtrationfiltered
concentrationconcentrated
customThe white solid residue was dried under vacuum

Sources & evidence

ORD record: ord-ea62c74a835d44c997a9628218a5822a
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09346852B2

Reaction notes

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