Water → HCID 67341780, compound

HRID 1907154Notes

Reaction equation

HRID 1907154 reaction equation
C[CH:2]([CH2:6][CH2:7][CH2:8][CH2:9][C@@H:10]([NH:23][C:24](=[O:44])[C@H:25]([CH2:34][C:35]1[C:40]([CH3:41])=[CH:39][C:38]([OH:42])=[CH:37][C:36]=1[CH3:43])[NH:26][C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[C:11](=[O:22])[NH:12][CH2:13][CH2:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:3]([OH:5])=[O:4].[OH-].[Li+].O>C1COCC1>[C:30]([O:29][C:27]([NH:26][C@H:25]([C:24]([NH:23][C@@H:10]([C:11](=[O:22])[NH:12][CH2:13][CH2:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH2:9][CH2:8][CH2:7][CH2:6][CH2:2][C:3]([OH:5])=[O:4])=[O:44])[CH2:34][C:35]1[C:40]([CH3:41])=[CH:39][C:38]([OH:42])=[CH:37][C:36]=1[CH3:43])=[O:28])([CH3:33])([CH3:31])[CH3:32]

Participants

5

Reactant 3

HCID 962WaterHCID 3939Lithium HydroxideHCID 67342264HCID 67342264, compound

Product 1

HCID 67341780HCID 67341780, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl (7R)-7-{[N-(tert-butoxycarbonyl)-2,6-dimethyl-L-tyrosyl]amino}-8-oxo-8-[(3-phenylpropyl)amino]octanoic acid (400 mg, 0.65 mmol) from preparation 14 in 3 ml dry THF was added a 0.5M solution of lithium hydroxide in water (3 ml, 1.5 mmol) and the reaction mixture stirred at rt overnight. Volatiles were evaporated and the residue acidified with 0.5M KHSO4. Product was extracted with ethyl acetate and the organic extract washed with brine, dried over MgSO4 and concentrated to a fine white solid which was taken directly into boc deprotection (preparation 28) on basis of LRMS m/z 598 [M+H].

Workup

  1. customVolatiles were evaporated
  2. extractionProduct was extracted with ethyl acetate
  3. extractionthe organic extract
  4. washwashed with brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated to a fine white solid which
  7. customwas taken directly into boc deprotection (preparation 28) on basis of LRMS m/z 598 [M+H]

Sources & evidence

ORD record
ord-c694192eb162495f89d0893a612dc0e1
Source dataset
uspto-grants-2013_12
Patent number
US08598123B2

Reaction notes

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