1-Chloro-2,4-Dinitrobenzene → (3S)-3-(5-Nitro-1H-benzimidazol-1-yl)-3-phenylpropanoic acid

HRID 1676082Notes

Reaction equation

HRID 1676082 reaction equation
N[C@H](C1C=CC=CC=1)CC(OC)=O.[N+:14]([C:17]1[CH:22]=[C:21]([N+:23]([O-:25])=[O:24])[CH:20]=[CH:19][C:18]=1Cl)([O-])=O.NC1C=CC=CC=1C(NC1C=CC2N=C[N:38]([CH:41]([C:46]3[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=3)[CH2:42][C:43]([OH:45])=[O:44])[C:37]=2C=1)=O>>[N+:23]([C:21]1[CH:20]=[CH:19][C:18]2[N:38]([C@H:41]([C:46]3[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=3)[CH2:42][C:43]([OH:45])=[O:44])[CH:37]=[N:14][C:17]=2[CH:22]=1)([O-:25])=[O:24]

Participants

4

Reactant 3

HCID 61-Chloro-2,4-DinitrobenzeneHCID 788099Methyl (S)-3-amino-3-phenylpropanoateHCID 116110403-{6-[(2-aminobenzoyl)amino]-1H-benzimidazol-1-yl}-3-phenylpropanoic acid

Product 1

HCID 58653644(3S)-3-(5-Nitro-1H-benzimidazol-1-yl)-3-phenylpropanoic acid

Procedure

Using a similar procedure to that described in Preparation 45, the title compound (19 mg) was prepared from methyl (3S)-3-amino-3-phenylpropanoate and 2,4-dinitrochlorobenzene, and liberated as the free acid using a procedure similar to that described in Preparation II. [LCMS (Method C, Mobile Phase I) RT=2.60 min, MH+ 312].

Workup

  1. customthat described in Preparation 45

Sources & evidence

ORD record
ord-2b7a3cd27c2442c8a74fda551fd43f23
Source dataset
uspto-grants-2011_08
Patent number
US08003806B2

Reaction notes

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