Water → HCID 85132509, compound

HRID 416521Notes

Reaction equation

[C:1]([O:5][C:6]([NH:8][CH2:9][CH:10](OS(C)(=O)=O)[CH3:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:17]([OH:20])(=[S:19])[CH3:18].C([O-])([O-])=O.[Cs+].[Cs+].O>CN(C=O)C>[C:1]([O:5][C:6]([NH:8][CH2:9][CH:10]([S:19][C:17](=[O:20])[CH3:18])[CH3:11])=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

Conditions

Temperature: 80 °C

Procedure

A solution of 11.9 g (47.0 mmol) crude methanesulfonic acid 2-tert-butoxycarbonylamino-1-methyl-ethyl ester in 100 ml DMF was added to a mixture of 5.0 g (1.4 equiv.) thioacetic acid and 15.3 g (1.0 equiv.) Cs2CO3 in 150 ml DMF. The reaction mixture was stirred for 4 h at 80° C. under argon and light protection. The mixture was poured into 300 ml water and extracted twice with 300 ml ethyl acetate each. 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: CH2Cl2) gave pure thioacetic acid S-(2-tert-butoxycarbonylamino-1-methyl-ethyl) ester as brown oil.

Workup

extractionextracted twice with 300 ml ethyl acetate each
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: CH2Cl2)

Sources & evidence

ORD record: ord-b9af6c3f6f94487d80a221adaaea3641
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08088925B2

Reaction notes

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