4-Methylmorpholine → HCID 9987417, compound

HRID 569139Notes

Reaction equation

HRID 569139 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1[S:10][CH:11]=[C:12]([C:14](=[CH:18][CH2:19][CH3:20])[C:15]([OH:17])=O)[N:13]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CS(Cl)(=O)=O.C1(C)C=CC(S(O)(=O)=O)=CC=1.[C:37]1([CH:43]([O:50][C:51]([C:53]2[N:58]3[C:59](=[O:62])[C@@H:60]([NH2:61])[C@H:57]3[S:56][CH2:55][C:54]=2[CH2:63][O:64][C:65](=[O:67])[NH2:66])=[O:52])[C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1.CN1CCOCC1>ClCCl.C(N(CC)CC)C>[C:37]1([CH:43]([O:50][C:51]([C:53]2[N:58]3[C:59](=[O:62])[C@@H:60]([NH:61][C:15](=[O:17])/[C:14](/[C:12]4[N:13]=[C:9]([NH:8][C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[S:10][CH:11]=4)=[CH:18]\[CH2:19][CH3:20])[C@H:57]3[S:56][CH2:55][C:54]=2[CH2:63][O:64][C:65](=[O:67])[NH2:66])=[O:52])[C:44]2[CH:45]=[CH:46][CH:47]=[CH:48][CH:49]=2)[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=1

Participants

7

Reactant 4

HCID 79724-MethylmorpholineHCID 31297Methanesulfonyl chlorideHCID 13127405HCID 13127405, compoundHCID 53400423HCID 53400423, compound

Product 1

HCID 9987417HCID 9987417, compoundYield 86.1%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8471TriethylamineSolvent

Procedure

To a mixture of 2-(2-t-butoxycarbonylaminothiazol-4-yl)-pentenoic acid (75 mg), triethylamine (0.041 ml), and dichloromethane (3 ml) is added dropwise methanesulfonyl chloride (0.02 ml) at -60° C. with stirring. After stirring at the same temperature for 5 hours, a solution of 7beta-amino-3-carbamoyloxymethyl-3-cephem-4-carboxylic acid diphenylmethyl ester p-toluenesulphonate salt (153 mg) and N-methylmorpholine (0.05 ml) in dichloromethane (3 ml) is added dropwise to the mixture. After stirring for 3.5 hours, the mixture is quenched with diluted hydrochloric acid. The organic layer is separated, washed with water, dried, and concentrated. The residue is purified by silica gel column chromatography to give 7beta-[(Z)-2-(2-t-butoxycarbonylaminothiazol-4-yl)-2-pentenoyl]amino-3-carbamoyloxymethyl-3-cephem-4-carboxylic acid diphenylmethyl ester (155 mg).

Workup

  1. stirringAfter stirring at the same temperature for 5 hours
  2. stirringAfter stirring for 3.5 hours
  3. customthe mixture is quenched with diluted hydrochloric acid
  4. customThe organic layer is separated
  5. washwashed with water
  6. customdried
  7. concentrationconcentrated
  8. customThe residue is purified by silica gel column chromatography

Sources & evidence

ORD record
ord-129bc46c2182477abfab43cbd09bc730
Source dataset
uspto-grants-1988_03
Patent number
US04731361

Reaction notes

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