Anisole → 7-[[[2-[(Diethoxyphosphinyl)-amino]-4-thiazolyl]-(methoxyimino)acetyl]amino]-3-[[(1-methyl-1H-tetrazol-5-yl)thio]methyl]-8-oxo-5 thia-1-azabicyclo[4.2.0]oct-2-ene2-carboxylic Acid

HRID 249107Notes

Reaction equation

HRID 249107 reaction equation
C(OP(NC1SC=C(/C(=N/OC)/C(O)=O)N=1)(OCC)=O)C.[CH2:22]([O:24][P:25]([NH:30][C:31]1[S:32][CH:33]=[C:34]([C:36](=[N:69][O:70][CH3:71])[C:37]([NH:39][CH:40]2[C:47](=[O:48])[N:46]3[CH:41]2[S:42][CH2:43][C:44]([CH2:61][S:62][C:63]2[N:67]([CH3:68])[N:66]=[N:65][N:64]=2)=[C:45]3[C:49]([O:51]CC2C=CC(OC)=CC=2)=[O:50])=[O:38])[N:35]=1)([O:27][CH2:28][CH3:29])=[O:26])[CH3:23].C1(OC)C=CC=CC=1>FC(F)(F)C(O)=O.C(=O)(O)[O-]>[CH2:28]([O:27][P:25]([NH:30][C:31]1[S:32][CH:33]=[C:34]([C:36](=[N:69][O:70][CH3:71])[C:37]([NH:39][CH:40]2[C:47](=[O:48])[N:46]3[CH:41]2[S:42][CH2:43][C:44]([CH2:61][S:62][C:63]2[N:67]([CH3:68])[N:66]=[N:65][N:64]=2)=[C:45]3[C:49]([OH:51])=[O:50])=[O:38])[N:35]=1)([O:24][CH2:22][CH3:23])=[O:26])[CH3:29]

Participants

6

Reactant 3

HCID 7519AnisoleHCID 15028031(2Z)-2-[2-(diethoxyphosphorylamino)-1,3-thiazol-4-yl]-2-methoxyiminoacetic acidHCID 867453597-[[[2-[(diethoxy-phosphinyl)amino]-4-thiazolyl]-(methoxyimino)acetyl]-amino]-3-[[(1-methyl-1H-tetrazol-5-yl)thio]methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, (4-methoxyphenyl)methyl ester

Product 1

HCID 566164277-[[[2-[(Diethoxyphosphinyl)-amino]-4-thiazolyl]-(methoxyimino)acetyl]amino]-3-[[(1-methyl-1H-tetrazol-5-yl)thio]methyl]-8-oxo-5 thia-1-azabicyclo[4.2.0]oct-2-ene2-carboxylic Acid

Reagents, catalysts & solvents 2

HCID 769Bicarbonate IonSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

The procedure of example 68 was repeated using 350 mg of [6R-[6-α, 7-β (Z)]]-7-[[[2-[(diethoxyphosphinyl)amino]-4-thiazolyl]-(methoxyimino)acetyl]amino]-3-[[(1-methyl-1H-tetrazol-5-yl)thio]methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, (4-methoxyphenyl)methyl ester and 0.075 ml anisole in trifluoroacetic acid for 5 minutes. The product was obtained by acidification in aqueous bicarbonate and extraction with methylene chloride in the pH range 3.2 to 3.0 to give 200 mg of the desired product; MS ((+) FAB), 648 (M+H); NMR (300 MHz, d6 -DMSO) δ 1.28 (t, 6, OCH2CH3), 3.71 (pair of doublets, 2, endocyclic-CH2S--), 3.85 (s, 3, NCH3), 3.97 (s, 3, OCH3), 4.07 (m, 4, CH2OP=O), 4.33 (m, 2, exocyclic-CH2S--) 5.01 (d, 1, 6H of 7-ACA), 5.79 (dd, 1, of 7-ACA), 7.19 (d, 1, NH).

Workup

  1. customfor 5 minutes
  2. extractionextraction with methylene chloride in the pH

Sources & evidence

ORD record
ord-dca01a537972494681749bbe459b71ad
Source dataset
uspto-grants-1993_05
Patent number
US05212291

Reaction notes

Loading…