Ethyl Acetate → 3(S)-[(Carbobenzyloxy)amino]-2,3-dihydro-1,5-benzothiazepin-4(5H)-one

HRID 53122Notes

Reaction equation

HRID 53122 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8][CH2:9][C@H:10]([C:22]([OH:24])=O)[NH:11][C:12]([O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:13].Cl.CN(C)CCCN=C=NCC.C(OCC)(=O)C>CN(C=O)C>[C:12]([NH:11][C@H:10]1[C:22](=[O:24])[NH:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=2[S:8][CH2:9]1)([O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:13]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 13375104S-(o-aminophenyl)-N-carbobenzyloxy-D-cysteine

Product 1

HCID 207031603(S)-[(Carbobenzyloxy)amino]-2,3-dihydro-1,5-benzothiazepin-4(5H)-oneYield 54%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 13.10 g (37.9 mmol) of S-(o-aminophenyl)-N-carbobenzyloxy-D-cysteine and 7.27 g (37.9 mmol) of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride in 82 mL of DMF was stirred at room temperature for 2 hours. To this solution was added 330 mL of ethyl acetate. The mixture was extracted 4 times with 200 mL of 1N NaOH. The ethyl acetate solution was dried with magnesium sulfate (MgSO4) and evaporated to a white amorphous residue. The residue was triturated with ether, and the resulting white crystals were filtered to yield 6.70 g (54%) of 3(S)-[(Carbobenzyloxy)amino]-2,3-dihydro-1,5-benzothiazepin-4(5H)-one as a white solid.

Workup

  1. extractionThe mixture was extracted 4 times with 200 mL of 1N NaOH
  2. dry with materialThe ethyl acetate solution was dried with magnesium sulfate (MgSO4)
  3. customevaporated to a white amorphous residue
  4. customThe residue was triturated with ether
  5. filtrationthe resulting white crystals were filtered

Sources & evidence

ORD record
ord-bee5f94e094841a3a51baed91aa2ce2c
Source dataset
uspto-grants-1997_04
Patent number
US05618808

Reaction notes

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