Pyridine → HCID 70620182, compound

HRID 1679193Notes

Reaction equation

HRID 1679193 reaction equation
[NH2:1][CH:2]1[C:27](=[O:28])[N:4]2[C:5]([C:14]([O:16][CH2:17][C:18]3[CH:23]=[CH:22][C:21]([N+:24]([O-:26])=[O:25])=[CH:20][CH:19]=3)=[O:15])=[C:6]([CH2:9][O:10][C:11](=[O:13])[CH3:12])[CH2:7][S:8][C@:3]12[O:29][CH3:30].N1C=CC=CC=1.[S:37]1[CH:41]=[CH:40][CH:39]=[C:38]1[CH2:42][C:43](Cl)=[O:44]>C(Cl)Cl>[S:37]1[CH:41]=[CH:40][CH:39]=[C:38]1[CH2:42][C:43]([NH:1][CH:2]1[C:27](=[O:28])[N:4]2[C:5]([C:14]([O:16][CH2:17][C:18]3[CH:23]=[CH:22][C:21]([N+:24]([O-:26])=[O:25])=[CH:20][CH:19]=3)=[O:15])=[C:6]([CH2:9][O:10][C:11](=[O:13])[CH3:12])[CH2:7][S:8][C@:3]12[O:29][CH3:30])=[O:44]

Participants

5

Reactant 3

HCID 1049PyridineHCID 1623622-Thiopheneacetyl chlorideHCID 70621000HCID 70621000, compound

Product 1

HCID 70620182HCID 70620182, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of the major isomer of p-nitrobenzyl 7-amino-6-methoxy-3-acetoxymethyl-ceph-3-em-4-carboxylate (53 mg., 0.12 mMol) in anhydrous CH2Cl2 (1 ml.) is cooled in an ice-bath and treated with pyridine (10.7 μl, 0.13 mMol) and 2-thienylacetyl chloride (17.8 μl., 0.13 mMol). The resulting solution is stirred in the cold for 30 mins., and then diluted with CH2Cl2, washed with H2O (3x) and brine, dried with MgSO4, filtered, and evaporated in vacuo. Crystallization of the residual yellow oil (66 mg.) from CH2Cl2 - hexane affords p-nitrobenzyl 7-(2-thienylacetamido)-6-methoxy-3-acetoxymethyl-ceph-3-em-4-carboxylate as off-white crystals: mp 148°-151° C.; ir (neat) 3.04, 5.57, 5.74, 5.91, 6.54, 7.40, 8.1, 11.67, and 13.5μ; nmr (CDCl3) δ 2.05 (s, 3, COCH3), 3.23 (s, 3, OCH3), 3.38 (s, 2, SCH2), 3.82 (s, 2, thienyl-CH2), 4.75, 5.10 (ABq, 2, J=13Hz, CH2OAc), 5.32 (d, 1, J=9Hz, H7), 5.35 (s, 2, CH2Ar), 6.82 (d, 1, J=9Hz, NH), 6.95 (m, 2, thienyl-H), 7.23 (m, 1, thienyl-H), and 7.53, 8.17 (ABq, 4, J=9Hz, ArH); mass spectrum m/e 561 (M+), 381, 365, 321, and 200.

Workup

  1. washwashed with H2O (3x) and brine
  2. dry with materialdried with MgSO4
  3. filtrationfiltered
  4. customevaporated in vacuo
  5. customCrystallization of the residual yellow oil (66 mg.) from CH2Cl2 - hexane

Sources & evidence

ORD record
ord-365dfc33bf964e9c948f5644ecb4ab38
Source dataset
uspto-grants-1978_03
Patent number
US04079179

Reaction notes

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