DL-valine → HCID 3326825, compound

HRID 1588861Notes

Reaction equation

CC1C=C([CH2+]=NC(C(O)=O)C(C)C)C=CC=1.[NH2:17][CH:18]([C:22]([OH:24])=[O:23])[CH:19]([CH3:21])[CH3:20].C(=O)([O-])O.[Na+].[CH3:30][C:31]1[CH:32]=[C:33]([N:37]=[C:38]=[O:39])[CH:34]=[CH:35][CH:36]=1>>[CH3:30][C:31]1[CH:32]=[C:33]([NH:37][C:38]([NH:17][CH:18]([C:22]([OH:24])=[O:23])[CH:19]([CH3:21])[CH3:20])=[O:39])[CH:34]=[CH:35][CH:36]=1

Participants

Reactant 3

HCID 1182DL-valine

HCID 69303m-Tolyl isocyanate

HCID 516892Sodium Bicarbonate

Product 1

HCID 3326825HCID 3326825, compound

Procedure

(RS)-N-(3-Methylphenylcarbamo-yl)valine may be prepared in a manner similar to that described in Example 35 for the preparation of (RS)-N-(3-methylphenylcarbamoyl)phenylglycine, but starting with (RS)-valine (4.7 g), sodium hydrogen carbonate (3.36 g) and 3-methylphenyl isocyanate (5.14 cc). (RS)-N-(3-Methylphenylcarbamoyl)valine (6.6 g), m.p. 170° C., is thereby obtained.

Sources & evidence

ORD record: ord-680f65c99273462d8c090205699552e0
Source dataset: uspto-grants-1993_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05223529

Reaction notes

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