Triethylamine → 4-Cyclopentyl-9-methoxy-1,4-benzothiazepine-2,5 (3H)-dione

HRID 67903Notes

Reaction equation

HRID 67903 reaction equation
[SH:1][C:2]1[C:19]([O:20][CH3:21])=[CH:18][CH:17]=[CH:16][C:3]=1[C:4]([N:6]([CH:11]1[CH2:15][CH2:14][CH2:13][CH2:12]1)[CH2:7][C:8](O)=[O:9])=[O:5].C(N(CC)CC)C.ClC(OCC)=O>C(Cl)Cl>[CH:11]1([N:6]2[C:4](=[O:5])[C:3]3[CH:16]=[CH:17][CH:18]=[C:19]([O:20][CH3:21])[C:2]=3[S:1][C:8](=[O:9])[CH2:7]2)[CH2:15][CH2:14][CH2:13][CH2:12]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 13599182N-(2-Mercapto-3-methoxybenzoyl)-N-cyclopentylglycine

Product 1

HCID 135991844-Cyclopentyl-9-methoxy-1,4-benzothiazepine-2,5 (3H)-dione

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N-(2-mercapto-3-methoxybenzoyl)-N-cyclopentylglycine (14.5 g, 0.0469 m) and triethylamine (4.7 g, 0.0469 m) in methylene chloride (500 ml) were cooled to 0° C., and ethyl chloroformate (5.1 g, 0.0469 m) was added over one minute. The mixture was stirred 2 hours at 0°-10° C., washed (water, then brine), dried (Na2SO4) and concentrated. HPLC purification using hexane/ethyl acetate (1/1) as eluent gave the desired product. Recrystallization from ethyl acetate provided 5.4 g analytically pure material (yield: 35%).

Workup

  1. washwashed (water
  2. dry with materialbrine), dried (Na2SO4)
  3. concentrationconcentrated
  4. customHPLC purification

Sources & evidence

ORD record
ord-76c9ece36f77462aae9f7aa84b813371
Source dataset
uspto-grants-1982_08
Patent number
US04347246

Reaction notes

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