(3S)-2-Oxo-3-tert-butoxycarbonylamino-2,3,4,5-tetrahydro-1H-1,5-benzodiazepine-1-acetic acid methyl ester → 2-tert-Butoxycarbonylamino-3-(3-nitropyridin-2-ylamino)propionic acid

HRID 363875Notes

Reaction equation

HRID 363875 reaction equation
C1(NC2CCCCC2)CCCCC1.C(O[C:22]([NH:24][CH2:25][CH:26]([NH:30][C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[C:27]([OH:29])=[O:28])=O)C1C=CC=CC=1.COC(=O)CN1C2C=CC=CC=2NC[C@H](NC(OC(C)(C)C)=O)C1=O.Cl[C:64]1([N+:70]([O-:72])=[O:71])[CH:69]=[CH:68][CH:67]=[N:66]C1>>[C:34]([O:33][C:31]([NH:30][CH:26]([CH2:25][NH:24][C:22]1[C:64]([N+:70]([O-:72])=[O:71])=[CH:69][CH:68]=[CH:67][N:66]=1)[C:27]([OH:29])=[O:28])=[O:32])([CH3:35])([CH3:36])[CH3:37]

Participants

4

Reactant 3

HCID 54305289(3S)-2-Oxo-3-tert-butoxycarbonylamino-2,3,4,5-tetrahydro-1H-1,5-benzodiazepine-1-acetic acid methyl esterHCID 667566683-Chloro-3-nitro pyridineHCID 70179098Dicyclohexylamine 3-(((benzyloxy)carbonyl)amino)-2-((tert-butoxycarbonyl)amino)propanoate

Product 1

HCID 184657932-tert-Butoxycarbonylamino-3-(3-nitropyridin-2-ylamino)propionic acid

Procedure

(2S) 2-tert-Butoxycarbonylamino-3-(3-nitropyridin-2-ylamino)propionic acid was prepared by a similar method as (2S) 2-tert-butoxycarbonylamino-3-(2-nitrophenyl-amino)propionic acid in Step A of the synthesis of 600a, except that 3-chloro-3-nitro pyridine was used instead of 2-fluoronitrobenzene, to give 4.05 g (64%) of a yellow solid.

Sources & evidence

ORD record
ord-173f75be78b2486592afa1abe125109b
Source dataset
uspto-grants-1999_02
Patent number
US05874424

Reaction notes

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