Trifluoroacetic acid → (6R)-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-3-(isothiocyanatomethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

HRID 329934Notes

Reaction equation

HRID 329934 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].C(N(CC)CC)C.[C:35](Cl)(Cl)=[S:36].C(O)(C(F)(F)F)=O>C(#N)C.O>[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][N:1]=[C:35]=[S:36])[CH2:4][S:5][C@H:6]23)=[O:26])[N:21]=1

Participants

7

Reactant 4

HCID 6422Trifluoroacetic acidHCID 8471TriethylamineHCID 10040ThiophosgeneHCID 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 88615122(6R)-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-3-(isothiocyanatomethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

To a solution of 3-aminomethyl-7-[2-(2-aminothiazol-4-yl)-2-((Z)-methoxyimino)acetamido]ceph-3-em-4-carboxylic acid (1.34 g.) in acetonitrile (100 ml.), water (30 ml.) and triethylamine (1.01 g.) at -15° was dropwise added thiophosgene (250 ul.). The mixture was stirred for 30 minutes at -15° and then the pH of the mixture was adjusted to 3-4 by addition of TFA. The solvent was evaporated and the residue purifed by HPLC using an aqueous ammonium carbonate buffer, pH 6-7/MeOH 70:30 v/v as eluant to give 7-[2-(2-aminothiazol-4-yl)-2-((Z)-methoxyimino)acetamido]3-isothiocyanatomethylceph-3-em-4-carboxylic acid having the following nmr in solvent B:--3.56 (d, 1 H); 3.84 (d, 1 H); 4.08 (s, 3 H); 4.6 (d, 1 H); 4.84 (d, 1 H); 5.3 (d, 1 H); 5.96 (d, 1 H); 7.14 (s, 1 H).

Workup

  1. customat -15°
  2. customThe solvent was evaporated

Sources & evidence

ORD record
ord-e7306f0f8368408cb78f8d126ba2126d
Source dataset
uspto-grants-1990_01
Patent number
US04894371

Reaction notes

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