Triethylamine → N(2,2,4,4-tetramethyltetrahydrothiophene-3-yl)-t-butoxycarbonyl-D-serine amide

HRID 462849Notes

Reaction equation

[C:1]([O:5][C:6]([NH:8][C@@H:9]([C:12]([OH:14])=O)[CH2:10][OH:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.ClC(OCC)=O.[NH2:28][CH:29]1[C:33]([CH3:35])([CH3:34])[CH2:32][S:31][C:30]1([CH3:37])[CH3:36]>C(OCC)(=O)C.O1CCCC1>[CH3:36][C:30]1([CH3:37])[CH:29]([NH:28][C:12](=[O:14])[C@@H:9]([CH2:10][OH:11])[NH:8][C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[C:33]([CH3:35])([CH3:34])[CH2:32][S:31]1

Participants

Conditions

Temperature: -20 °C

Procedure

To a solution of 2.26 g. (11 mmole) of N-t-butoxycarbonyl-D-serine in 75 ml. of tetrahydrofuran is added 1.47 ml. (10 mmole) of triethylamine and the mixture cooled to -10° C. At this temperature is added 0.96 ml. (10 mmole) of ethyl chloroformate and stirring continued for 15 minutes. After cooling to -20° C., 1.6 g. (10 mmole) of dl-3-amino-2,2,4,4-tetramethyltetrahydrothiophene is added and the resulting mixture is allowed to warm to room temperature. Ethyl acetate is added and the mixture is washed twice with 50 ml. portions of 5% (by weight) aqueous citric acid, aqueous sodium bicarbonate (1×50 ml.) and saturated brine (1×50 ml.). The organic layer is dried (Na2SO4) and evaporated to dryness at reduced pressure to afford N(2,2,4,4-tetramethyltetrahydrothiophene-3-yl)-t-butoxycarbonyl-D-serine amide. This product is used without further purification in the next step. ##STR120##

Workup

additionAt this temperature is added 0.96 ml
temperatureto warm to room temperature
washthe mixture is washed twice with 50 ml
dry with materialThe organic layer is dried (Na2SO4)
customevaporated to dryness at reduced pressure

Sources & evidence

ORD record: ord-cd3b2df9bf8449e3b864b3f8197fb70c
Source dataset: uspto-grants-1985_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04517379

Reaction notes

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