Sodium Hydroxide → HCID 9850091, compound

HRID 1352088Notes

Reaction equation

HRID 1352088 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-482a98b663ab4ce28a345590603cdad9
Source dataset
uspto-grants-2007_05
Patent number
US07217728B2

Reaction notes

Loading…