Triphenylphosphine → HCID 86742762, compound

HRID 1382693Notes

Reaction equation

HRID 1382693 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([C:13]([OH:15])=O)[C@@H:10]([CH3:12])O)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:16](=[N:29][NH2:30])([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C(OC(N1C2C(=CC=CC=2)C=CC1OCC)=O)C.N(C(OCC)=O)=NC(OCC)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>>[C:17]1([C:16](=[N:29][N:30]2[C:13](=[O:15])[C@@H:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:2])([CH3:3])[CH3:4])[C@@H:10]2[CH3:12])[C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

6

Reactant 5

HCID 11776TriphenylphosphineHCID 278332-Ethoxy-1-(ethoxycarbonyl)-1,2-dihydroquinolineHCID 79304DiphenylmethylidenehydrazineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 2724766N-tert-Butoxycarbonyl-L-threonine

Product 1

HCID 86742762HCID 86742762, compound

Procedure

Also in accordance with Scheme 1 and starting with the reaction of t-butyloxycarbonyl-L-threonine (1b) with benzophenone hydrazone (2) in the presence of 2-ethoxy-1(2H)-quinolinecarboxylic acid ethyl ester the hydrazide derivative N-(t-butyloxycarbonyl)-L-threonine-2-(2-diphenylmethylene)hydrazide (3b) was obtained. Ring closure of (3b) as described above with diethyl azodicarboxylate and triphenylphosphine gave the β-lactam, t-butyl (S)-[1-[(diphenylmethylene)amino]-2-(S)-methyl-4-oxo-3-azetidinyl)-carbamate (4b). Catalytic hydrogenation of (4b) gave the N-amino compound t-butyl 1-amino-2-(S)-methyl-4-oxo-3-(S)-azetidinylcarbamate (5b) which was reacted with benzyl glyoxylate (6) to give the imino derivative benzyl [[4(S)-methyl-3(S)-[(t-butoxycarbonyl)amino]-2-oxo]imino]acetate (7b). Catalytic reduction of (7b) gave the amino derivative 4(S)-methyl-[[3(S)-[[(t-butyloxycarbonyl]amino]-2-oxo-1-azetidinyl]imino]acetic acid (8b) which was treated with trifluoroacetic acid to give the amino acid, [[(S)-3-amino-4-oxo-2-(S)-methyl-1-azetidinyl]iminoacetic acid trifluoroacetate (9b). Then condensation of the trimethylsilyl derivative (10b) with the activated ester of 2-(2-amino-4-thiazolyl)-2-methoxyiminoacetic acid (11) gave the desired monobactam derivative (S)-3-[2-(2-amino-4-thiazolyl)]-(Z)-2-methoxyiminoacetylamino-2-(S)-methyl-4-oxo-1-azetidinyliminoacetic acid (12b). ##STR3##

Workup

  1. customwas obtained

Sources & evidence

ORD record
ord-802e15d728d44d3ab6ae1b199dcc161c
Source dataset
uspto-grants-1989_02
Patent number
US04808579

Reaction notes

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