Sodium Carbonate → HCID 22840213, compound

HRID 868242Notes

Reaction equation

HRID 868242 reaction equation
[NH2:1][C@H:2]1[CH2:8][S:7][C@H:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH2:5][N:4]([CH2:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[C:3]1=[O:23].Br[CH:25]([CH2:31][CH2:32][CH2:33][CH2:34][N:35]1[C:39](=[O:40])[C:38]2=[CH:41][CH:42]=[CH:43][CH:44]=[C:37]2[C:36]1=[O:45])[C:26]([O:28][CH2:29][CH3:30])=[O:27].C(=O)([O-])[O-].[Na+].[Na+]>>[CH2:29]([O:28][C:26]([CH:25]([NH:1][C@H:2]1[CH2:8][S:7][C@H:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH2:5][N:4]([CH2:15][C:16]([O:18][C:19]([CH3:20])([CH3:22])[CH3:21])=[O:17])[C:3]1=[O:23])[CH2:31][CH2:32][CH2:33][CH2:34][N:35]1[C:39](=[O:40])[C:38]2=[CH:41][CH:42]=[CH:43][CH:44]=[C:37]2[C:36]1=[O:45])=[O:27])[CH3:30]

Participants

4

Reactant 3

HCID 10340Sodium CarbonateHCID 13605303HCID 13605303, compoundHCID 14423826HCID 14423826, compound

Product 1

HCID 22840213HCID 22840213, compound

Procedure

By following the same procedure as described in Example 4, a condensation reaction was carried out between 336 mg of t-butyl rel-α-[6(R)-amino-5-oxo-2(R)-phenylperhydro-1,4-thiazepin-4-yl]acetate and 552 mg of ethyl 2-bromo-6-phthalimidohexanoate in the presence of 318 mg of sodium carbonate to give two diastereoisomers. These isomers were separated by column chromatography through silica gel using a mixture of cyclohexane and ethyl acetate in the ratio 5:1 by volume as the eluent.

Workup

  1. customa condensation reaction
  2. customto give two diastereoisomers
  3. customThese isomers were separated by column chromatography through silica gel using
  4. additiona mixture of cyclohexane and ethyl acetate in the ratio 5:1 by volume as the eluent

Sources & evidence

ORD record
ord-380a2a17a1b44087884d52c4e88d565d
Source dataset
uspto-grants-1988_10
Patent number
US04778790

Reaction notes

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