Hydrochloric Acid → Methyl (S)-N-{2-butyl-1-[(2'-carboxybiphenyl-4-yl)methyl]-4-hydroxymethylimidazole-5-carbonyl}prolinate

HRID 52946

Reaction equation

HRID 52946 reaction equation
C([O:5][C:6]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[C:14]1[CH:19]=[CH:18][C:17]([CH2:20][N:21]2[C:25]([C:26](ON3C(=O)CCC3=O)=[O:27])=[C:24]([CH2:36][OH:37])[N:23]=[C:22]2[CH2:38][CH2:39][CH2:40][CH3:41])=[CH:16][CH:15]=1)=[O:7])(C)(C)C.Cl.[NH:43]1[CH2:51][CH2:50][CH2:49][C@H:44]1[C:45]([O:47][CH3:48])=[O:46].Cl>C(N(CC)CC)C>[CH2:38]([C:22]1[N:21]([CH2:20][C:17]2[CH:16]=[CH:15][C:14]([C:9]3[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=3[C:6]([OH:7])=[O:5])=[CH:19][CH:18]=2)[C:25]([C:26]([N:43]2[CH2:51][CH2:50][CH2:49][C@H:44]2[C:45]([O:47][CH3:48])=[O:46])=[O:27])=[C:24]([CH2:36][OH:37])[N:23]=1)[CH2:39][CH2:40][CH3:41]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 2733200methyl L-prolinate hydrochlorideHCID 19036239Succinimido 1-[(2'-t-butoxycarbonylbiphenyl-4-yl)methyl]-2-butyl-4-hydroxymethylimidazole-5-carboxylate

Product 1

HCID 86750660Methyl (S)-N-{2-butyl-1-[(2'-carboxybiphenyl-4-yl)methyl]-4-hydroxymethylimidazole-5-carbonyl}prolinate

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

Following a procedure similar to that described in Example 53, but using 529 mg of succinimido 1-[(2'-t-butoxycarbonylbiphenyl-4-yl)methyl]-2-butyl-4-hydroxymethylimidazole-5-carboxylate [prepared as described in Example 52(a)], 180 mg of methyl (S)-prolinate hydrochloride and 0.2 ml of triethylamine, 0.39 g of the hydrochloride of the title compound was obtained as an amorphous powder, melting at above 120° C. (with softening).

Sources & evidence

ORD record
ord-aaf7d1644c424ae1ba62d2ee987270db
Source dataset
uspto-grants-1997_04
Patent number
US05616599

Linked notes

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