Pyridine → HCID 70507631, compound

HRID 2296561Notes

Reaction equation

C(Cl)Cl.[OH:4][CH:5]1[C@@H:9]2[CH:10]([NH:13][C:14](=[O:23])[CH2:15][O:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[C:11](=[O:12])[N:8]2[CH:7]([C:24]([O:26][CH:27]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)=[O:25])[CH:6]1[CH3:40].N1C=CC=CC=1.[C:47](OC(=O)C)(=[O:49])[CH3:48]>CN(C)C1C=CN=CC=1.C(OCC)(=O)C.C(Cl)(Cl)Cl>[C:47]([O:4][CH:5]1[C@@H:9]2[CH:10]([NH:13][C:14](=[O:23])[CH2:15][O:16][C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)[C:11](=[O:12])[N:8]2[CH:7]([C:24]([O:26][CH:27]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)=[O:25])[CH:6]1[CH3:40])(=[O:49])[CH3:48]

Participants

Conditions

Temperature: -10 °C

Procedure

The washed, dried methylene chloride solution of benzhydryl 1-hydroxy-2-methyl-6-(2-phenoxyacetamido)carbapenam-3-carboxylate, freshly prepared according to Example 22 was cooled to -10° C. Pyridine (22 mg., 0.28 mmole), acetic anhydride (29 mg., 0.28 mmole) and 4-dimethylaminopyridine (3.4 mg., 0.028 mmoles) were added in sequence. After stirring for 1 hour at -10° C., tlc (4:1 chloroform:ethyl acetate) indicated acetylation was complete. The reaction mixture was evaporated to dryness in vacuo with toluene chases. Chromatography on silica gel using a methylene chloride-ethyl acetate gradient (0 to 7.5% ethyl acetate) afforded benzhydryl 1-acetoxy-2-methyl-6-(2-phenoxyacetamido)carbapenam-3-carboxylate [18 mg.; Rf 0.56 (4:1 chloroform:ethyl acetate; ir (CHCl3) 1780, 1730, 1680 cm-1 ].

Workup

customThe reaction mixture was evaporated to dryness in vacuo with toluene chases

Sources & evidence

ORD record: ord-9a6b4c5d98b747a38fc06a59ff66f58d
Source dataset: uspto-grants-1984_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04429128

Reaction notes

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