Formic Acid → HCID 177715839, compound

HRID 329933Notes

Reaction equation

HRID 329933 reaction equation
[NH2:1][CH2:2][C:3]1[CH2:4][S:5][C@@H:6]2[CH:13]([NH:14][C:15](=[O:26])/[C:16](/[C:20]3[N:21]=[C:22]([NH2:25])[S:23][CH:24]=3)=[N:17]\[O:18][CH3:19])[C:12](=[O:27])[N:7]2[C:8]=1[C:9]([OH:11])=[O:10].Cl[C:29]1[N:30]([CH3:50])[N:31]=[C:32]([O:36][CH:37]([C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)[C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[C:33](=[O:35])[N:34]=1.C(N(CC)CC)C.C(O)=O>CN(C=O)C>[NH2:25][C:22]1[S:23][CH:24]=[C:20](/[C:16](=[N:17]/[O:18][CH3:19])/[C:15]([NH:14][CH:13]2[C:12](=[O:27])[N:7]3[C:8]([C:9]([OH:11])=[O:10])=[C:3]([CH2:2][NH:1][C:29]4[N:30]([CH3:50])[N:31]=[C:32]([O:36][CH:37]([C:38]5[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=5)[C:44]5[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=5)[C:33](=[O:35])[N:34]=4)[CH2:4][S:5][C@H:6]23)=[O:26])[N:21]=1

Participants

6

Reactant 4

HCID 284Formic AcidHCID 8471TriethylamineHCID 198704012,5-Dihydro-3-chloro-6-diphenylmethoxy-2-methyl-5-oxo-1,2,4-triazineHCID 88601874(6R)-3-(aminomethyl)-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

Product 1

HCID 177715839HCID 177715839, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 3-aminomethyl-7-[2-(2-aminothiazol-4-yl)-2-((Z)-methoxyimino)acetamido]ceph-3-em-4-carboxylic acid (200 mg.), 2,5-dihydro-3-chloro-6-diphenylmethoxy-2-methyl-5-oxo-1,2,4-triazine (160 mg.) was triethylamine (200 ul.) in DMF (4 ml.) at 0° was allowed to stand for 3.5 hours. Formic acid (1 ml.) was added and the solvent was evaporated to give 7-[2-(2-aminothiazol-4-yl)-2-((Z)-methoxyimino)acetamido]-3-[(2,5-dihydro-6-diphenylmethoxy-2-methyl-5-oxo-1,2,4-triazin-3-yl)aminomethyl]ceph-3-em-4-carboxylic acid which was used without further purification. nmr in solvent B:--3.52 (s, 3 H); 3.6 (s, 2 H); 4.04 (s, 3 H); 4.4 (s, 2 H); 5.18 (d, 1 H); 5.84 (d, 1 H); 7.1 (s, 1 H).

Workup

  1. customat 0°
  2. customthe solvent was evaporated

Sources & evidence

ORD record
ord-92b3357d96f64a7ba5d8f0cc693ab717
Source dataset
uspto-grants-1990_01
Patent number
US04894371

Reaction notes

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