4-Methylmorpholine → HCID 131717512, compound

HRID 1885270Notes

Reaction equation

HRID 1885270 reaction equation
C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH3:12][O:13][C:14]1[CH:35]=[CH:34][C:17]([CH2:18][O:19][C:20]([C:22]2[N:27]3[C:28](=[O:31])[C@@H:29]([NH2:30])[C@H:26]3[S:25][CH2:24][C:23]=2[CH2:32][Cl:33])=[O:21])=[CH:16][CH:15]=1.[C:36]([O:40][C:41]([NH:43][C:44]1[S:45][CH:46]=[C:47]([C:49](=[N:53][O:54][C:55]([C:58]([O:60][C:61]([CH3:64])([CH3:63])[CH3:62])=[O:59])([CH3:57])[CH3:56])[C:50](O)=[O:51])[N:48]=1)=[O:42])([CH3:39])([CH3:38])[CH3:37].CN1CCOCC1.P(OCl)(OCl)(OC1C=CC=CC=1)=O>ClCCl.C(N(CC)CC)C>[C:36]([O:40][C:41]([NH:43][C:44]1[S:45][CH:46]=[C:47]([C:49](=[N:53][O:54][C:55]([C:58]([O:60][C:61]([CH3:64])([CH3:63])[CH3:62])=[O:59])([CH3:56])[CH3:57])[C:50]([NH:30][C@@H:29]2[C:28](=[O:31])[N:27]3[C:22]([C:20]([O:19][CH2:18][C:17]4[CH:16]=[CH:15][C:14]([O:13][CH3:12])=[CH:35][CH:34]=4)=[O:21])=[C:23]([CH2:32][Cl:33])[CH2:24][S:25][C@H:26]23)=[O:51])[N:48]=1)=[O:42])([CH3:39])([CH3:37])[CH3:38]

Participants

7

Reactant 4

HCID 79724-MethylmorpholineHCID 11390866HCID 11390866, compoundHCID 14032023HCID 14032023, compoundHCID 53651853HCID 53651853, compound

Product 1

HCID 131717512HCID 131717512, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

7β-Amino-3-chloromethyl-3-cephem-4-carboxylic acid p-methoxy-benzyl ester p-toluenesulfonate in dichloromethane is treated with triethylamine, 2-(2-t-butoxycarbonylamino-4-thiazolyl)-2-(1-t-butoxycarbonyl-1-methylethoxyimino)acetic acid, N-methylmorpholine, and phenyl dichloro phosphate to give p-methoxybenzyl 7β-[2-(2-t-butoxycarbonylamino-4-thiazolyl)-2-(1-t-butoxycarbonyl-1-methylethoxyimino)acetamido]-3-chloromethyl-3-cephem-4-carboxylate.

Sources & evidence

ORD record
ord-f99cd99ff87342acaf115130e62459b9
Source dataset
uspto-grants-1992_09
Patent number
US05143910

Reaction notes

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