Acetic Acid → 5-t-butoxycarbonylmethyl-3-(1-ethoxycarbonylethylamino)-2,3-dihydro-1,5-benzothiazepin-4(5H)-one

HRID 1719121Notes

Reaction equation

HRID 1719121 reaction equation
[NH2:1][CH:2]1[C:8](=[O:9])[N:7]([CH2:10][C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[C:6]2[CH:18]=[CH:19][CH:20]=[CH:21][C:5]=2[S:4][CH2:3]1.[C:22]([O:27][CH2:28][CH3:29])(=[O:26])[C:23]([CH3:25])=O.C(O)(=O)C.[BH]C#N.[Na]>C(O)C>[C:14]([O:13][C:11]([CH2:10][N:7]1[C:6]2[CH:18]=[CH:19][CH:20]=[CH:21][C:5]=2[S:4][CH2:3][CH:2]([NH:1][CH:23]([C:22]([O:27][CH2:28][CH3:29])=[O:26])[CH3:25])[C:8]1=[O:9])=[O:12])([CH3:16])([CH3:17])[CH3:15]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 12041Ethyl pyruvateHCID 134545423-amino-5-t-butoxycarbonylmethyl-2,3-dihydro-1,5-benzothiazepin-4(5H)-oneHCID 131714321Sodium boron cyanide hydride

Product 1

HCID 134707795-t-butoxycarbonylmethyl-3-(1-ethoxycarbonylethylamino)-2,3-dihydro-1,5-benzothiazepin-4(5H)-oneYield 50.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

1.5 g of 3-amino-5-t-butoxycarbonylmethyl-2,3-dihydro-1,5-benzothiazepin-4(5H)-one and 2.0 g of ethyl pyruvate were dissolved in 15 ml of ethanol. After the addition of 0.3 ml of acetic acid, the resulting mixture was stirred for 2 hours. Then, a solution of 420 mg of sodium boron cyanide hydride in 8 ml of ethanol was slowly added dropwise thereto. After this mixture was allowed to stand overnight, the solvent was distilled off under reduced pressure and the residue was dissolved in ethyl acetate. The resulting solution was washed with water, dried and then concentrated. The residue was purified by silica gel column chromatography using a 3:1 mixture of benzene and ethyl acetate as the eluent. Thus, there was obtained 1.0 g of the desired compound in the form of an oily material.

Workup

  1. waitto stand overnight
  2. distillationthe solvent was distilled off under reduced pressure
  3. dissolutionthe residue was dissolved in ethyl acetate
  4. washThe resulting solution was washed with water
  5. customdried
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel column chromatography
  8. additiona 3:1 mixture of benzene and ethyl acetate as the eluent

Sources & evidence

ORD record
ord-ba28893f3ca540019988b35937d0af92
Source dataset
uspto-grants-1985_09
Patent number
US04539150

Reaction notes

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