Sodium Carbonate → HCID 54370832, compound

HRID 868240Notes

Reaction equation

HRID 868240 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][CH2:35][CH2:36][NH:37][C:38]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39])[C:26]([O:28][CH2:29][CH3:30])=[O:27].C(=O)([O-])[O-].[Na+].[Na+]>>[C:41]([O:40][C:38]([NH:37][CH2:36][CH2:35][CH2:34][CH2:33][CH2:32][CH2:31][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])[C:26]([O:28][CH2:29][CH3:30])=[O:27])=[O:39])([CH3:44])([CH3:43])[CH3:42]

Participants

4

Reactant 3

HCID 10340Sodium CarbonateHCID 14423826HCID 14423826, compoundHCID 21287859HCID 21287859, compound

Product 1

HCID 54370832HCID 54370832, compound

Procedure

By following the same procedure as described in Example 4, a condensation reaction was carried out between 400 mg of t-butyl rel-α-[6(R)-amino-5-oxo-2(R)-phenylperhydro-1,4-thiazepin-4-yl]acetate and 1.08 g of ethyl 2-bromo-8-t-butoxycarbonylaminooctanoate in the presence of 0.76 g of sodium carbonate to give two diastereoisomers. These isomers were separated by column chromatography through silica gel, using a mixture of methylene chloride and ethyl acetate in the ratio 10:1 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
  4. additiona mixture of methylene chloride and ethyl acetate in the ratio 10:1 by volume as the eluent

Sources & evidence

ORD record
ord-6caac778ea0c47bd84a6d0f9a29c779f
Source dataset
uspto-grants-1988_10
Patent number
US04778790

Reaction notes

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