Water → HCID 86621467, compound

HRID 416538Notes

Reaction equation

[CH2:1]([O:8][C:9](=[O:29])[CH2:10][CH:11](OS(C)(=O)=O)[CH2:12][NH:13][C:14]([O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:30]([O-:33])(=[S:32])[CH3:31].[K+].CCN(C(C)C)C(C)C.O>CN(C=O)C>[CH2:1]([O:8][C:9](=[O:29])[CH2:10][CH:11]([S:32][C:30](=[O:33])[CH3:31])[CH2:12][NH:13][C:14]([O:16][CH2:17][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)=[O:15])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 250 mg (0.59 mmol) 4-benzyloxycarbonylamino-3-methanesulfonyloxy-butyric acid benzyl ester in 5 ml DMF were added sequentially 68 mg (1.0 equiv.) potassium thioacetate and 101 μl (1.0 equiv.) DIPEA. The reaction mixture was stirred for 2 h at 80° C. under argon and light protection. Further 68 mg (1.0 equiv.) potassium thioacetate and 101 μl (1.0 equiv.) DIPEA were added. After stirring for another 2 h at 80° C., the mixture was poured into 10 ml water and extracted three times with 15 ml ethyl acetate. The combined organic layers were washed with brine, dried over anhydrous MgSO4 and concentrated under reduced pressure. Purification by flash chromatography on silica gel (eluent: heptane/ethyl acetate) gave pure 3-acetylsulfanyl-4-benzyloxycarbonylamino-butyric acid benzyl ester as yellow oil.

Workup

stirringAfter stirring for another 2 h at 80° C.
extractionextracted three times with 15 ml ethyl acetate
washThe combined organic layers were washed with brine
dry with materialdried over anhydrous MgSO4
concentrationconcentrated under reduced pressure
customPurification by flash chromatography on silica gel (eluent: heptane/ethyl acetate)

Sources & evidence

ORD record: ord-05b9745e3c4343719066c496ddd8dcdb
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08088925B2

Reaction notes

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