Triethylamine → t-Butyl alpha-{6(R)-[1(S)-ethoxycarbonyl-3-phenylpropylamino]-5-oxo-2-(2-thienyl)perhydro-1,4-thiazepin-4-yl}acetate

HRID 256083Notes

Reaction equation

HRID 256083 reaction equation
[C:1]1([CH2:7][CH2:8][C@@H:9](OS(C(F)(F)F)(=O)=O)[C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2:23][C@H:24]1[CH2:30][S:29][CH:28]([C:31]2[S:32][CH:33]=[CH:34][CH:35]=2)[CH2:27][N:26]([CH2:36][C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])[C:25]1=[O:44].C(N(CC)CC)C>C(Cl)Cl>[CH2:13]([O:12][C:10]([C@@H:9]([NH:23][C@H:24]1[CH2:30][S:29][CH:28]([C:31]2[S:32][CH:33]=[CH:34][CH:35]=2)[CH2:27][N:26]([CH2:36][C:37]([O:39][C:40]([CH3:42])([CH3:41])[CH3:43])=[O:38])[C:25]1=[O:44])[CH2:8][CH2:7][C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)=[O:11])[CH3:14]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10860745Ethyl (2R)-4-phenyl-2-[(trifluoromethanesulfonyl)oxy]butanoateHCID 18610546HCID 18610546, compound

Product 1

HCID 18610544t-Butyl alpha-{6(R)-[1(S)-ethoxycarbonyl-3-phenylpropylamino]-5-oxo-2-(2-thienyl)perhydro-1,4-thiazepin-4-yl}acetateYield 88.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 4.0 g of ethyl 4-phenyl-2-(R)-trifluoromethanesulfonyloxybutyrate in 15 ml of methylene chloride was added dropwise to a solution of 4.0 g of t-butyl α-[6(R)-amino-5-oxo-2-(2-thienyl)perhydro-1,4-thiazepin-4-yl]acetate [prepared as described in step (g) above] and 1.62 ml of triethylamine in 50 ml of methylene chloride. The reaction mixture was stirred for 2 hours at room temperature, after which it was washed with water and dried over anhydrous magnesium sulfate; the solvent was then evaporated off under reduced pressure. The residue was purified by silica gel column chromatography, using a 20:1 by volume mixture of methylene chloride and ethyl acetate as the eluent, to give 5.5 g of the title compound in the form of a syrup.

Workup

  1. washafter which it was washed with water
  2. dry with materialdried over anhydrous magnesium sulfate
  3. customthe solvent was then evaporated off under reduced pressure
  4. customThe residue was purified by silica gel column chromatography
  5. additionby volume mixture of methylene chloride and ethyl acetate as the eluent

Sources & evidence

ORD record
ord-5eb7963387d94bd78523d140d917f1a1
Source dataset
uspto-grants-1987_10
Patent number
US04699905

Reaction notes

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