Sodium Chloride → HCID 20164963, compound

HRID 256045Notes

Reaction equation

HRID 256045 reaction equation
[NH2:1][CH:2]1[CH2:8][S:7][CH:6]([C:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH:12]=[CH:11][CH:10]=2)[CH2:5][N:4]([CH2:19][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[C:3]1=[O:27].Br[CH:29]([CH2:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)[CH2:30][C:31]([O:33][CH2:34][CH3:35])=[O:32].C(=O)([O-])[O-].[Na+].[Na+].[Cl-].[Na+]>CN(C)C=O.C(OCC)(=O)C>[CH2:34]([O:33][C:31]([CH:30]([NH:1][CH:2]1[CH2:8][S:7][CH:6]([C:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH:12]=[CH:11][CH:10]=2)[CH2:5][N:4]([CH2:19][C:20]([O:22][C:23]([CH3:24])([CH3:26])[CH3:25])=[O:21])[C:3]1=[O:27])[CH2:29][CH2:36][C:37]1[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=1)=[O:32])[CH3:35]

Participants

7

Reactant 4

HCID 5234Sodium ChlorideHCID 10340Sodium CarbonateHCID 20164914HCID 20164914, compoundHCID 20164978HCID 20164978, compound

Product 1

HCID 20164963HCID 20164963, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of a mixture of 803 g of t-butyl α-[6-amino-2-(1-naphthyl)-5-oxoperhydro-1,4-thiazepin-4-yl]acetate [prepared as described in step (g) above] and 1.13 g of ethyl 3-bromo-4-phenylbutyrate in 10 ml of dimethylformamide was added 0.66 g of sodium carbonate. The reaction mixture was stirred at 80° C. for 15 hours and then dissolved in a mixture of ethyl acetate and an aqueous solution of sodium chloride. The ethyl acetate layer was separated, washed with water and dried over anhydrous magnesium sulfate, and the solvent was then evaporated off. The residue was subjected to silica gel column chromatography using a 1:30 by volume mixture of ethyl acetate and methylene chloride as eluent, which separated the product into two isomers, A and B, (ascribed to the asymmetric carbon atom to which the phenethyl group is attached).

Workup

  1. customThe ethyl acetate layer was separated
  2. washwashed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was then evaporated off
  5. additionby volume mixture of ethyl acetate and methylene chloride as eluent
  6. customwhich separated the product into two isomers

Sources & evidence

ORD record
ord-e36f68f8969a4ea89556924241caa3a5
Source dataset
uspto-grants-1987_10
Patent number
US04699905

Reaction notes

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