Dimethyl Sulfoxide → tert-Butyl 6-oxohexylcarbamate

HRID 2247817Notes

Reaction equation

C(Cl)(=O)C(Cl)=O.CS(C)=O.[C:11]([NH:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][OH:25])([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12].C(N(CC)CC)C>C(Cl)Cl.O>[C:11]([NH:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH:24]=[O:25])([O:13][C:14]([CH3:15])([CH3:16])[CH3:17])=[O:12]

Participants

Conditions

Temperature: 20 °C

Procedure

To a stirred solution of 5.3 mL (7.71 g, 60.7 mmoles) oxalyl chloride in 100 mL methylene choride at -70° C. under argon was added 8.6 mL (10.23 g, 121.5 mmoles) dimethyl sulfoxide in 30 mL methylene chloride. After 2 min. a solution of 12 g (55.2 mmoles) of (6) in 50 mL methylene chloride was added over 5 min. After 20 min. 38.5 mL (27.9 g, 276 mmoles) triethylamine was added. After 10 min. more, the mixture was allowed to warm to 20° C. and 250 mL water was added. After separation, the aqueous layer was extracted again with methylene chloride and the combined organic layers were washed with brine and dried over sodium sulfate. After evaporation in vacuo, the residue was chromatographed (Flash, hexane - ethyl acetate, 7:3) to provide 11.36 g of a pale yellow oil (7).

Workup

waitAfter 10 min. more
customAfter separation
extractionthe aqueous layer was extracted again with methylene chloride
washthe combined organic layers were washed with brine
dry with materialdried over sodium sulfate
customAfter evaporation in vacuo
customthe residue was chromatographed (Flash, hexane - ethyl acetate, 7:3)

Sources & evidence

ORD record: ord-5b980011d20a44eeaa48766e7e0b6944
Source dataset: uspto-grants-1991_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05037808

Reaction notes

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