Methanol → HCID 22172613, compound

HRID 1823683Notes

Reaction equation

HRID 1823683 reaction equation
CO.C[O:4][C:5](=[O:30])[C:6]1[C:11]([NH:12][C:13](=[O:29])[CH:14]([NH:18][C:19]([O:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[O:20])[CH:15]([CH3:17])[CH3:16])=[CH:10][CH:9]=[N:8][CH:7]=1.[OH-].[Na+]>O>[CH2:22]([O:21][C:19]([NH:18][CH:14]([CH:15]([CH3:17])[CH3:16])[C:13]([NH:12][C:11]1[C:6]([C:5]([OH:30])=[O:4])=[CH:7][N:8]=[CH:9][CH:10]=1)=[O:29])=[O:20])[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 69314204HCID 69314204, compound

Product 1

HCID 22172613HCID 22172613, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Formula 507 where R1, R3 and R4 are H; R6 is Isopropyl; R6′ is H; W, Y and Z are —C═; and X is —N═: To a solution of MeOH and H2O (2:1, 150 mL) and 4-(2-benzyloxycarbonylamino-3-methyl-butyrylamino)-nicotinic acid methyl ester (10.5 g, 27.2 mmol) was added sodium hydroxide (2.18 g, 54.5 mmol). The mixture was stirred for 1 hour, after which silica gel (20 g) was added into the solution. After letting this mixture stir for 10 minutes, the silica gel was filtered off and the solvents were evaporated under reduced pressure. The corresponding carboxylic acid of Formula 507, 4-(2-benzyloxycarbonylamino-3-methyl-butyrylamino)-nicotinic acid (10.0 g, 99%) was obtained in sufficient purity to be carried forward for use in the next step. MS (Cl) M/E: 372.3.

Workup

  1. additionafter which silica gel (20 g) was added into the solution
  2. stirringstir for 10 minutes
  3. filtrationthe silica gel was filtered off
  4. customthe solvents were evaporated under reduced pressure

Sources & evidence

ORD record
ord-673aaf8a85494378aefd522848b8f995
Source dataset
uspto-grants-2006_05
Patent number
US07038048B2

Reaction notes

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