Methyl L-phenylalaninate hydrochloride → HCID 67858686, compound

HRID 2254291Notes

Reaction equation

HRID 2254291 reaction equation
Cl.C[O:3]C(=O)[C@H](CC1C=CC=CC=1)N.COC(=O)[C@H](CC1C=CC=CC=1)N[C:20]([CH2:22][C:23]1[N:27]([CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=2[Cl:35])[C:26]([CH2:36][CH2:37][CH2:38][CH3:39])=[N:25][CH:24]=1)=[O:21]>>[ClH:35].[CH2:36]([C:26]1[N:27]([CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=2[Cl:35])[C:23]([CH2:22][C:20]([OH:21])=[O:3])=[CH:24][N:25]=1)[CH2:37][CH2:38][CH3:39]

Participants

3

Reactant 2

HCID 75736Methyl L-phenylalaninate hydrochlorideHCID 67858908HCID 67858908, compound

Product 1

HCID 67858686HCID 67858686, compound

Procedure

The procedure of Example 12 (ii-iii) was followed using L-phenylalanine methyl ester hydrochloride in place of glycine methyl ester hydrochloride. From 5.59 g (16.3 mmol) of 2-[2-n-butyl-1-{(2-chlorophenyl)methyl}-1H-imidazol-5-yl]acetic acid hydrochloride, there was obtained 6.88 g (90%) of the intermediate N-[{2-n-butyl-1-(2-chlorophenyl)methyl-1H-imidazol-5-yl}methylcarbonyl]-L-phenylalanine methyl ester; mp 88°-90° C. (from ethanol/water). Hydrolysis of this ester provided the title compound in a 79% yield; mp 168°-170° C.; [α]25 (c=1, methanol).

Sources & evidence

ORD record
ord-4cfe3e49113f43d9a0f51a56b0ee039b
Source dataset
uspto-grants-1993_08
Patent number
US05234917

Reaction notes

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