Lithium Hydroxide → HCID 86585059, compound

HRID 1264407Notes

Reaction equation

HRID 1264407 reaction equation
C[O:2][C:3](=[O:37])[C@@H:4]([NH:15][C:16]([C@@H:18]1[CH2:22][C@H:21]([SH:23])[CH2:20][N:19]1[S:24]([C:27]1[CH:36]=[CH:35][C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[CH:28]=1)(=[O:26])=[O:25])=[O:17])[CH2:5][C:6]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[NH:8][CH:7]=1.[Li+].[OH-].C(S)[C@@H](O)[C@H](O)CS>C1COCC1>[NH:8]1[C:9]2[C:14](=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:6]([CH2:5][C@H:4]([NH:15][C:16]([C@@H:18]2[CH2:22][C@H:21]([SH:23])[CH2:20][N:19]2[S:24]([C:27]2[CH:36]=[CH:35][C:34]3[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=3)[CH:28]=2)(=[O:26])=[O:25])=[O:17])[C:3]([OH:37])=[O:2])=[CH:7]1

Participants

5

Reactant 3

HCID 3939Lithium HydroxideHCID 446094D-1,4-DithiothreitolHCID 86585060HCID 86585060, compound

Product 1

HCID 86585059HCID 86585059, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

243 mg (4.5 mmol) (S)-3-(1H-Indol-3-yl)-2-[[(2S,4S)-4-mercapto-1-(naphthalene-2-sulfonyl)-pyrrolidine-2-carbonyl]-amino]-propionic acid methyl ester in 13.5 ml THF were treated 22.5 ml 0.1M LiOH in the presence of 209 mg (13.5 mmol) DTT at RT for 72h. The solution was acidified with 1MKHSO4KHS04 and the inorganic phase was extracted with EtOAc. The combined organic phases were washed with brine and were dried with Na2SO4. Column chromatography with CH2Cl2:MeOH 9:1, followed by trituration with hexane yielded 204 mg (86%) (S)-3-(1H-Indol-3-yl)-2-[[(2S,4S)-4-mercapto-1-(naphthalene-2-sulfonyl)-pyrrolidine-2-carbonyl]-amino]-propionic acid as white solid, mp 130° C., MS: 522 (M-H)−.

Workup

  1. extractionthe inorganic phase was extracted with EtOAc
  2. washThe combined organic phases were washed with brine
  3. dry with materialwere dried with Na2SO4

Sources & evidence

ORD record
ord-2f3c540ac3254ba3b304ff126226df56
Source dataset
uspto-grants-2003_04
Patent number
US06541638B2

Reaction notes

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