Dimethyl Sulfoxide → 2(S)-Tert-butoxycarbonylamino-6-triisopropylsilyloxy-4,4-dimethyl-hexanal

HRID 863211Notes

Reaction equation

CS(C)=O.C(Cl)(=O)C(Cl)=O.[C:11]([O:15][C:16]([NH:18][C@@H:19]([CH2:22][C:23]([CH3:38])([CH3:37])[CH2:24][CH2:25][O:26][Si:27]([CH:34]([CH3:36])[CH3:35])([CH:31]([CH3:33])[CH3:32])[CH:28]([CH3:30])[CH3:29])[CH2:20][OH:21])=[O:17])([CH3:14])([CH3:13])[CH3:12].S([O-])(O)(=O)=O.[K+]>C(Cl)Cl.C(N(CC)CC)C>[C:11]([O:15][C:16]([NH:18][C@@H:19]([CH2:22][C:23]([CH3:37])([CH3:38])[CH2:24][CH2:25][O:26][Si:27]([CH:28]([CH3:30])[CH3:29])([CH:31]([CH3:32])[CH3:33])[CH:34]([CH3:35])[CH3:36])[CH:20]=[O:21])=[O:17])([CH3:14])([CH3:13])[CH3:12]

Participants

Conditions

Temperature: -10 °C

Procedure

14.7 ml of dimethylsulfoxide in 200 ml of methylene chloride are added dropwise to a solution of 13.4 ml of oxalyl chloride in 200 ml of methylene chloride at -60° C. After 15 min, a solution of 43.2 g of 2(S)-tert-butoxycarbonylamino-6-triisopropylsilyloxy-4,4-dimethyl-hexan-1-ol in 320 ml of methylene chloride is added dropwise at -60° C. in the course of 40 min, while stirring vigorously. 58 ml of triethylamine are then added and the reaction mixture is stirred at -60° C. for 90 min. It is allowed to warm to -10° C., 200 ml of a 20% potassium hydrogen sulfate solution are added, the mixture is subsequently stirred briefly and the product is extracted with methylene chloride. This gives 43 g of the title compound, which is reacted further without additional purification: Rf (A)=0.62, Rf (D)=0.3; Rt (II)=34.8 min.

Workup

stirringthe reaction mixture is stirred at -60° C. for 90 min
stirringthe mixture is subsequently stirred briefly
extractionthe product is extracted with methylene chloride
customThis gives 43 g of the title compound, which is reacted further without additional purification

Sources & evidence

ORD record: ord-d276592d366e4f0da127ecb57491d959
Source dataset: uspto-grants-1998_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05719141

Reaction notes

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