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Lithium hydroxide, monohydrate → N-[2,6-dichloro-4-[[[(1R)-1-(1-naphthalenyl)ethyl]amino]carbonyl]benzoyl]-3-[(thiophene-2-carbonyl)amino]-L-alanine

HRID 1726805
Notes
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Reaction equation

HRID 1726805 reaction equation
O.[OH-].[Li+].[Cl:4][C:5]1[CH:27]=[C:26]([C:28]([NH:30][C@@H:31]([C:33]2[C:42]3[C:37](=[CH:38][CH:39]=[CH:40][CH:41]=3)[CH:36]=[CH:35][CH:34]=2)[CH3:32])=[O:29])[CH:25]=[C:24]([Cl:43])[C:6]=1[C:7]([NH:9][C@H:10]([C:20]([O:22]C)=[O:21])[CH2:11][NH:12][C:13]([C:15]1[S:16][CH:17]=[CH:18][CH:19]=1)=[O:14])=[O:8]>O.O1CCCC1.CO>[Cl:4][C:5]1[CH:27]=[C:26]([C:28]([NH:30][C@@H:31]([C:33]2[C:42]3[C:37](=[CH:38][CH:39]=[CH:40][CH:41]=3)[CH:36]=[CH:35][CH:34]=2)[CH3:32])=[O:29])[CH:25]=[C:24]([Cl:43])[C:6]=1[C:7]([NH:9][C@H:10]([C:20]([OH:22])=[O:21])[CH2:11][NH:12][C:13]([C:15]1[S:16][CH:17]=[CH:18][CH:19]=1)=[O:14])=[O:8]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 131723047N-[2,6-dichloro-4-[[[(1R)-1-(1-naphthalenyl) ethyl]amino]carbonyl]benzoyl]-3-[(thiophene-2-carbonyl)amino]-L-alanine, methyl ester

Product 1

HCID 54166190N-[2,6-dichloro-4-[[[(1R)-1-(1-naphthalenyl)ethyl]amino]carbonyl]benzoyl]-3-[(thiophene-2-carbonyl)amino]-L-alanineYield 67%

Reagents, catalysts & solvents 3

HCID 887
Methanol
Solvent
HCID 962WaterSolvent
HCID 8028TetrahydrofuranSolvent

Procedure

A solution of lithium hydroxide monohydrate (100 mg, 2.38 mmol) in water (5 mL) was added to a solution of N-[2,6-dichloro-4-[[[(1R)-1-(1-naphthalenyl)ethyl]amino]carbonyl]benzoyl]-3-[(thiophene-2-carbonyl)amino]-L-alanine, methyl ester (260 mg, 0.434 mmol) in tetrahydrofuran (15 mL) and methanol (5 mL), and the resulting mixture was stirred at room temperature overnight. The solution was evaporated, and the residue was partitioned between ethyl acetate (40 mL) and 1 M HCl (10 mL). The organic layer was evaporated and the residue was dissolved in methanol (˜1 mL), purified by HPLC, and lyophilized to give N-[2,6-dichloro-4-[[[(1R)-1-(1-naphthalenyl)ethyl]amino]carbonyl]benzoyl]-3-[(thiophene-2-carbonyl)amino]-L-alanine (170 mg, 67%).

Workup

  1. customThe solution was evaporated
  2. customthe residue was partitioned between ethyl acetate (40 mL) and 1 M HCl (10 mL)
  3. customThe organic layer was evaporated
  4. dissolutionthe residue was dissolved in methanol (˜1 mL)
  5. custompurified by HPLC

Sources & evidence

ORD record
ord-36807a0ca11245bb819a3bda79f7e237
Source dataset
uspto-grants-2009_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07491741B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes