Sodium Chloride → HCID 18610541, compound

HRID 256007Notes

Reaction equation

HRID 256007 reaction equation
C(=O)([O-])[O-].[Na+].[Na+].[NH2:7][C@H:8]1[CH2:14][S:13][CH2:12][C@@H:11]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[N:10]([CH2:21][C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[C:9]1=[O:29].BrC(CC[CH2:39][CH2:40][C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1)C(OCC)=O.[Cl-].[Na+].[C:49]([O:52][CH2:53][CH3:54])(=[O:51])[CH3:50]>CN(C)C=O>[CH2:53]([O:52][C:49]([C@H:50]([NH:7][C@H:8]1[CH2:14][S:13][CH2:12][C@@H:11]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[N:10]([CH2:21][C:22]([O:24][C:25]([CH3:26])([CH3:28])[CH3:27])=[O:23])[C:9]1=[O:29])[CH2:39][CH2:40][C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1)=[O:51])[CH3:54]

Participants

7

Reactant 5

HCID 5234Sodium ChlorideHCID 8857Ethyl AcetateHCID 10340Sodium CarbonateHCID 18610548HCID 18610548, compoundHCID 20164911HCID 20164911, compound

Product 1

HCID 18610541HCID 18610541, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
65 °C

Procedure

2.4 g of sodium carbonate were added to a mixture of 1.1 g of t-butyl α-[6(R)-amino-5-oxo-3(R)-phenylperhydro-1,4-thiazepin-4-yl]acetate [prepared as described in step (g) above]]and 1.4 g of ethyl 2-bromo-4-phenethylbutyrate dissolved in 15 ml of dimethylformamide, and this mixture was stirred for 15 hours at 65° C. The reaction mixture was then dissolved in ethyl acetate and an aqueous sodium chloride solution. The ethyl acetate layer was separated, washed with water and dried over anhydrous magnesium sulfate, after which the solvent was removed by distillation. The residue was subjected to silica gel column chromatography, using a 1:9 by volume mixture of ethyl acetate and methylene chloride as eluent. t-Butyl α-[6(R)-[1(R)-ethoxycarbonyl-3-phenylpropylamino]-5-oxo-3(R)-phenylperhydro-1,4-thiazepin-4-yl]acetate was obtained from the first fraction as an oily substance in a yield of 0.53 g.

Workup

  1. customprepared
  2. customThe ethyl acetate layer was separated
  3. washwashed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customafter which the solvent was removed by distillation
  6. additionby volume mixture of ethyl acetate and methylene chloride as eluent

Sources & evidence

ORD record
ord-2eb44a241ec5406f84a944f8326d80f5
Source dataset
uspto-grants-1987_10
Patent number
US04699905

Reaction notes

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