Lithium Hydroxide → HCID 22876407, compound

HRID 2394099Notes

Reaction equation

HRID 2394099 reaction equation
[C:1]([NH:8][C@H:9]([C@H:17]1[O:21][C:20](=[O:22])[C@H:19]([CH2:23][C:24]2[CH:29]=[CH:28][C:27]([S:30]([CH2:33][C:34]3[C:39]([Cl:40])=[CH:38][CH:37]=[CH:36][C:35]=3[Cl:41])(=[O:32])=[O:31])=[CH:26][CH:25]=2)[CH2:18]1)[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[OH-:42].[Li+]>C(COC)OC>[C:1]([NH:8][C@@H:9]([CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C@@H:17]([OH:42])[CH2:18][C@@H:19]([CH2:23][C:24]1[CH:29]=[CH:28][C:27]([S:30]([CH2:33][C:34]2[C:39]([Cl:40])=[CH:38][CH:37]=[CH:36][C:35]=2[Cl:41])(=[O:31])=[O:32])=[CH:26][CH:25]=1)[C:20]([OH:21])=[O:22])([O:3][C:4]([CH3:5])([CH3:6])[CH3:7])=[O:2]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 67709378HCID 67709378, compound

Product 1

HCID 22876407HCID 22876407, compound

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

In analogy with Example 5e), 6.7 g (10.83 mmol) of 5(S)-[1(S)-(Boc-amino)-2-phenylethyl]-3(R)-{[p-(2,6-dichlorobenzylsulfonyl)phenyl]methyl}dihydrofuran-2-(3H)-one in 170 ml of dimethoxyethane are hydrolysed with 43.3 ml of a 1M lithium hydroxide solution (RT, 17 h). Partitioning between 3× methylene chloride, NH4Cl/citric acid solution and saline, and stirring the crude product in ether, affords the title compound: tRet (II)=15.5 min.

Workup

  1. customPartitioning between 3× methylene chloride, NH4Cl/citric acid solution and saline

Sources & evidence

ORD record
ord-4c2976e014c54c39929c502de934e05e
Source dataset
uspto-grants-1998_09
Patent number
US05807891

Reaction notes

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