Dicyclohexylcarbodiimide → (Hexahydro-5-oxo-1,4-thiazepin-6-yl)carbamic acid, (1,1-dimethylethyl) ester

HRID 1981888Notes

Reaction equation

HRID 1981888 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([C:15]([OH:17])=O)[CH2:10][S:11][CH2:12][CH2:13][NH2:14])=[O:7])([CH3:4])([CH3:3])[CH3:2].ON1C(=O)CCC1=O.C1(N=C=NC2CCCCC2)CCCCC1>CN(C=O)C>[C:1]([O:5][C:6]([NH:8][CH:9]1[CH2:10][S:11][CH2:12][CH2:13][NH:14][C:15]1=[O:17])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 80170N-HydroxysuccinimideHCID 22946527N-t-Butoxycarbonyl-S-(2-aminoethyl)-L-cysteine

Product 1

HCID 15591256(Hexahydro-5-oxo-1,4-thiazepin-6-yl)carbamic acid, (1,1-dimethylethyl) esterYield 66.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

N-t-Butoxycarbonyl-S-(2-aminoethyl)-L-cysteine (5.0 g) and N-hydroxysuccinimide (2.6 g) are dissolved in 500 ml of DMF. With cooling in an ice-bath, a solution of dicyclohexylcarbodiimide (4.7 g) in 10 ml of DMF is added dropwise over a period of 15 minutes. The reaction mixture is kept in a 4° room for 10 days. The solvent is then removed by lyophilization. The crude product is extracted into chloroform. Repeated chromatography on silica gel (20:1 chloroform-methanol) affords the pure product (3.1 g). The NMR spectrum is consistent with the assigned structure. A pure sample is obtained by recrystallization (ether-methanol) and analyzes for C10H18N2O3S.

Workup

  1. temperatureWith cooling in an ice-bath
  2. customis kept in a 4°
  3. customfor 10 days
  4. customThe solvent is then removed by lyophilization
  5. extractionThe crude product is extracted into chloroform

Sources & evidence

ORD record
ord-b6f72876ef574db99345f0d7bafcf8e1
Source dataset
uspto-grants-1986_06
Patent number
US04594341

Reaction notes

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