Lithium Hydroxide → HCID 21947233, compound

HRID 2361576Notes

Reaction equation

HRID 2361576 reaction equation
C[O:2][C:3]([CH:5]1[CH2:9][C:8]2([S:14][CH2:13][CH2:12][CH2:11][S:10]2)[CH2:7][N:6]1[C:15](=[O:40])[CH:16]([NH:21][C:22](=[O:39])[CH:23]([CH:33]1[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34]1)[NH:24][C:25]([C:27]1[CH:32]=[N:31][CH:30]=[CH:29][N:28]=1)=[O:26])[C:17]([CH3:20])([CH3:19])[CH3:18])=[O:4].[Li+].[OH-]>C1COCC1.O>[CH:33]1([CH:23]([NH:24][C:25]([C:27]2[CH:32]=[N:31][CH:30]=[CH:29][N:28]=2)=[O:26])[C:22]([NH:21][CH:16]([C:17]([CH3:19])([CH3:20])[CH3:18])[C:15]([N:6]2[CH:5]([C:3]([OH:4])=[O:2])[CH2:9][C:8]3([S:10][CH2:11][CH2:12][CH2:13][S:14]3)[CH2:7]2)=[O:40])=[O:39])[CH2:34][CH2:35][CH2:36][CH2:37][CH2:38]1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 21054032HCID 21054032, compound

Product 1

HCID 21947233HCID 21947233, compound

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

Ester 33 (50 mg) in THF-water (400 uL-100 uL) was treated with LiOH (7 mg) and the mixture stirred for 3 hours at room temperature. The mixture was evaporated, diluted with EtOAc, washed with 1.0N HCl and brine then dried over magnesium sulfate, filtered, and concentrated in vacuo to give 2-[2-{2-cyclohexyl-2-[(pyrazine-2-carbonyl)-amino]-acetylamino}-3,3-dimethyl-butyryl)-6,10-dithia-2-aza-spiro[4.5]decane-3-carboxylic acid 34 as a white solid which was used in the next step without further purification. Mass Spec. MH+=578.0, MH−=576.2.

Workup

  1. customThe mixture was evaporated
  2. additiondiluted with EtOAc
  3. washwashed with 1.0N HCl and brine
  4. dry with materialthen dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-183f608e651048d0b24404faa3cf6fef
Source dataset
uspto-grants-2014_04
Patent number
US08691758B2

Reaction notes

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