Sodium → HCID 11214642, compound

HRID 1828085Notes

Reaction equation

HRID 1828085 reaction equation
[C:1]([OH:4])(=[O:3])[CH3:2].C([O:7][C:8](=[O:40])[CH2:9][O:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[C:17]1[C:21]([CH3:22])=[CH:20][N:19]([CH:23]([C:27](=[O:39])[NH:28][CH2:29][C:30]2[CH:35]=[CH:34][C:33]([C:36](=[NH:38])[NH2:37])=[CH:32][CH:31]=2)[O:24][CH2:25][CH3:26])[N:18]=1)C.[Na].CCOC(C)=O.CC(C)=O.O.CC(O)=O>C(O)C.O>[C:1]([OH:4])(=[O:3])[CH3:2].[C:36]([C:33]1[CH:32]=[CH:31][C:30]([CH2:29][NH:28][C:27]([CH:23]([O:24][CH2:25][CH3:26])[N:19]2[CH:20]=[C:21]([CH3:22])[C:17]([C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=3[O:10][CH2:9][C:8]([OH:40])=[O:7])=[N:18]2)=[O:39])=[CH:35][CH:34]=1)(=[NH:37])[NH2:38]

Participants

5

Reactant 3

HCID 5360545SodiumHCID 11168880HCID 11168880, compoundHCID 86598840HCID 86598840, compound

Product 1

HCID 11214642HCID 11214642, compoundYield 74.5%

Reagents, catalysts & solvents 1

HCID 19096565Water ethanolSolvent

Procedure

To a stirred mixture of (RS)-(2-{1-[(4-carbamimidoyl-benzylcarbamoyl)-ethoxy-methyl]-4-methyl-1H-pyrazol-3-yl}-phenoxy)-acetic acid ethyl ester acetate (82 mg) at r.t. in ethanol/H2O 1:1 (2 ml) was added sodium hydroxyde (20 mg). Stirring was then continued for 2 h. The mixture was concentrated to leave an off-white paste. The crude product was isolated by chromatography (silica gel, EtOAc/acetone/H2O/HOAc 6:2:1:1) to give (RS)-(2-{1-[(4-carbamimidoyl-benzylcarbamoyl)-ethoxy-methyl]-4-methyl-1H-pyrazol-3-yl}-phenoxy)-acetic acid acetate (58 mg) as an off-white solid. MS 466.4 ([M+H]+)

Workup

  1. concentrationThe mixture was concentrated
  2. customto leave an off-white paste

Sources & evidence

ORD record
ord-3c1c7f740a0447c597ce3f989dc3cf11
Source dataset
uspto-grants-2006_06
Patent number
US07056932B2

Reaction notes

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