Sodium Hydroxide → HCID 9850091, compound

HRID 1726798Notes

Reaction equation

HRID 1726798 reaction equation
[OH-].[Na+].[Cl:3][C:4]1[CH:26]=[C:25]([C:27]([NH:29][CH2:30][C:31]2[CH:36]=[CH:35][CH:34]=[C:33]([O:37]C(C3C=CSC=3)=O)[CH:32]=2)=[O:28])[CH:24]=[C:23]([Cl:45])[C:5]=1[C:6]([NH:8][C@H:9]([C:19]([O:21]C)=[O:20])[CH2:10][NH:11][C:12]([C:14]1[CH:18]=[CH:17][S:16][CH:15]=1)=[O:13])=[O:7].ClC1C=C(C(NCC2C=CC=C(O)C=2)=O)C=C(Cl)C=1C(N[C@H](C(OC)=O)CNC(C1C=CSC=1)=O)=O>CO>[Cl:3][C:4]1[CH:26]=[C:25]([C:27]([NH:29][CH2:30][C:31]2[CH:36]=[CH:35][CH:34]=[C:33]([OH:37])[CH:32]=2)=[O:28])[CH:24]=[C:23]([Cl:45])[C:5]=1[C:6]([NH:8][C@H:9]([C:19]([OH:21])=[O:20])[CH2:10][NH:11][C:12]([C:14]1[CH:18]=[CH:17][S:16][CH:15]=1)=[O:13])=[O:7]

Participants

5

Reactant 3

HCID 14798Sodium Hydroxide2×HCID 131723043HCID 131723043, compoundHCID 131724620HCID 131724620, compound

Product 1

HCID 9850091HCID 9850091, compoundYield 130.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

An aqueous solution of sodium hydroxide (1 M; 0.305 Ml, 0.305 mmol) was added to a solution of N-[2,6-dichloro-4-[[[[3-[(thiophene-3-carbonyl)oxy]phenyl]methyl]amino]carbonyl]benzoyl]-3-[(thiophene-3-carbonyl)amino]-L-alanine, methyl ester (101 mg, 0.153 mmol) in methanol (2 Ml). The solution was allowed to stir overnight and then concentrated. An aqueous solution of sodium hydroxide (1 M; 0.210 Ml, 0.210 mmol) was added to a solution of N-[2,6-dichloro-4-[[[(3-hydroxyphenyl)methyl]amino]carbonyl]-benzoyl]-3-[(thiophene-3-carbonyl)amino]-L-alanine, methyl ester (58 mg, 0.105 mmol) in methanol (2 Ml). The solution was allowed to stir overnight and then concentrated. The residues from the two reactions were purified by HPLC and lyophilized to give N-[2,6-dichloro-4-[[[(3-hydroxyphenyl)methyl]amino]carbonyl]-benzoyl]-3-[(thiophene-3-carbonyl)amino]-L-alanine (107 mg, 78%) as a white solid.

Workup

  1. concentrationconcentrated
  2. stirringto stir overnight
  3. concentrationconcentrated
  4. customThe residues from the two reactions were purified by HPLC

Sources & evidence

ORD record
ord-ea8f1e4f55204433ac1d53d84ef40fa1
Source dataset
uspto-grants-2009_02
Patent number
US07491741B2

Reaction notes

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