Hydrochloric Acid → 4-{4-[({[5-Amino-2-(cyclopropylsulfanyl)phenyl]methyl}(methyl)carbamoyl)[(1-{bis[(tert-butoxy)carbonyl]amino}-4-fluoroisoquinolin-6-yl)amino]methyl]-2,6-dimethylphenyl}-3-hydroxybutanoic acid

HRID 708815Notes

Reaction equation

HRID 708815 reaction equation
[Li+].[OH-].[NH2:3][C:4]1[CH:5]=[CH:6][C:7]([S:59][CH:60]2[CH2:62][CH2:61]2)=[C:8]([CH2:10][N:11]([CH3:58])[C:12]([CH:14]([NH:31][C:32]2[CH:33]=[C:34]3[C:39](=[CH:40][CH:41]=2)[C:38]([N:42]([C:50]([O:52][C:53]([CH3:56])([CH3:55])[CH3:54])=[O:51])[C:43]([O:45][C:46]([CH3:49])([CH3:48])[CH3:47])=[O:44])=[N:37][CH:36]=[C:35]3[F:57])[C:15]2[CH:20]=[C:19]([CH3:21])[C:18]([CH2:22][CH:23]([OH:29])[CH2:24][C:25]([O:27]C)=[O:26])=[C:17]([CH3:30])[CH:16]=2)=[O:13])[CH:9]=1.Cl>C1COCC1>[NH2:3][C:4]1[CH:5]=[CH:6][C:7]([S:59][CH:60]2[CH2:61][CH2:62]2)=[C:8]([CH2:10][N:11]([CH3:58])[C:12]([CH:14]([NH:31][C:32]2[CH:33]=[C:34]3[C:39](=[CH:40][CH:41]=2)[C:38]([N:42]([C:50]([O:52][C:53]([CH3:54])([CH3:55])[CH3:56])=[O:51])[C:43]([O:45][C:46]([CH3:48])([CH3:49])[CH3:47])=[O:44])=[N:37][CH:36]=[C:35]3[F:57])[C:15]2[CH:16]=[C:17]([CH3:30])[C:18]([CH2:22][CH:23]([OH:29])[CH2:24][C:25]([OH:27])=[O:26])=[C:19]([CH3:21])[CH:20]=2)=[O:13])[CH:9]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 118093103Methyl 4-{4-[({[5-amino-2-(cyclopropylsulfanyl)phenyl]methyl}(methyl)carbamoyl)[(1 {bis[(tert-butoxy)carbonyl]amino}-4-fluoroisoquinolin-6-yl)amino]methyl]-2,6-dimethylphenyl}-3-hydroxybutanoate

Product 1

HCID 1180928014-{4-[({[5-Amino-2-(cyclopropylsulfanyl)phenyl]methyl}(methyl)carbamoyl)[(1-{bis[(tert-butoxy)carbonyl]amino}-4-fluoroisoquinolin-6-yl)amino]methyl]-2,6-dimethylphenyl}-3-hydroxybutanoic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1.0 M LiOH (0.266 mL, 0.266 mmol) was added to a solution of 2D (225 mg, 0.266 mmol) in THF (2 mL) and stirred for 6 h at rt. HCl (0.266 mL, 1 M) was added and the mixture was extracted with EtOAc. The combined organics were washed with brine, dried over Na2SO4 and concentrated in vacuo. The product 2E was used without further purification. MS (ESI) m/z: 832.7 (M+H)+.

Workup

  1. extractionthe mixture was extracted with EtOAc
  2. washThe combined organics were washed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. customThe product 2E was used without further purification

Sources & evidence

ORD record
ord-2b3f917c36d64adfac1c6b330a0ea420
Source dataset
uspto-grants-2015_11
Patent number
US09174974B2

Reaction notes

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