Lithium Hydroxide → HCID 88100944, compound

HRID 1264419Notes

Reaction equation

HRID 1264419 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[S:11]([N:14]1[C@H:18]([C:19]([N:21]2[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]2)=[O:20])[CH2:17][C@H:16]([S:27]C(=O)C)[CH2:15]1)(=[O:13])=[O:12].[Li+].[OH-]>C1COCC1>[SH:27][C@@H:16]1[CH2:15][N:14]([S:11]([C:2]2[CH:3]=[CH:4][C:5]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[CH:1]=2)(=[O:12])=[O:13])[C@H:18]([C:19]([N:21]2[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]2)=[O:20])[CH2:17]1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 131723839HCID 131723839, compound

Product 1

HCID 88100944HCID 88100944, compoundYield 74.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

148 mg (0.33 mmol) (3S,5S)-Thioacetic acid S-[1-(naphthalene-2-sulfonyl)-5-(piperidine-1-carbonyl)-pyrrolidin-3-yl] ester in 9 ml THF were treated with 9 ml 0.1M LiOH for 30 min at 0° C. and 1h at RT. The solution was extracted with ether, the inorganic phase was acidified with 1M KHSO4 and extracted with EtOAc. The EtOAc phase was washed with brine and dried over Na2SO4, trituration with hexane gave 99 mg (74%) (2S,4S)-[4-Mercapto-1-(naphthalene-2-sulfonyl)-pyrrolidin-2-yl]-piperidin-1-yl-methanone as white solid, MS: 405 (MH+).

Workup

  1. customat RT
  2. extractionThe solution was extracted with ether
  3. extractionextracted with EtOAc
  4. washThe EtOAc phase was washed with brine
  5. dry with materialdried over Na2SO4, trituration with hexane

Sources & evidence

ORD record
ord-c6773c117c5642199b1527b7803d58f1
Source dataset
uspto-grants-2003_04
Patent number
US06541638B2

Reaction notes

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