Triethylamine → HCID 16162312, compound

HRID 483034Notes

Reaction equation

HRID 483034 reaction equation
C(NC1SC=C(/C(=N/O[C:32]([C:45]2[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=2)([C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)/C(O)=O)N=1)(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.ON1[C:56]2[CH:57]=[CH:58][CH:59]=[CH:60][C:55]=2N=N1.C1(N=C=N[CH:70]2[CH2:75][CH2:74][CH2:73][CH2:72][CH2:71]2)CCCCC1.N[C@@H:77]1[C:95](=O)N2C(C(O)=O)=C(CSN3CN(N)N=N3)CS[C@H:78]12.C(N(CC)CC)C.[NH2:104][C:105]1[S:106][CH:107]=[C:108](/[C:110](=[N:134]/[O:135][CH2:136][CH2:137][CH2:138][CH3:139])/[C:111]([NH:113][C@@H:114]2[C:132](=[O:133])[N:116]3[C:117]([C:129]([OH:131])=[O:130])=[C:118]([CH2:121][S:122][C:123]4[N:127]([NH2:128])[N:126]=[N:125][N:124]=4)[CH2:119][S:120][C@H:115]23)=[O:112])[N:109]=1>CC(N(C)C)=O.O>[C:32]([NH:104][C:105]1[S:106][CH:107]=[C:108](/[C:110](=[N:134]/[O:135][C:136]([C:55]2[CH:56]=[CH:57][CH:58]=[CH:59][CH:60]=2)([C:70]2[CH:71]=[CH:72][CH:73]=[CH:74][CH:75]=2)[C:137]2[CH:95]=[CH:77][CH:78]=[CH:139][CH:138]=2)/[C:111]([NH:113][C@@H:114]2[C:132](=[O:133])[N:116]3[C:117]([C:129]([OH:131])=[O:130])=[C:118]([CH2:121][S:122][C:123]4[N:127]([NH2:128])[N:126]=[N:125][N:124]=4)[CH2:119][S:120][C@H:115]23)=[O:112])[N:109]=1)([C:45]1[CH:46]=[CH:47][CH:48]=[CH:49][CH:50]=1)([C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)[C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1

Participants

9

Reactant 6

HCID 8471TriethylamineHCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 10327150(Z)-2-(Trityloxyimino)-2-[2-(tritylamino)thiazol-4-yl]acetic AcidHCID 886759677beta-amino-3-[(1-amino-1H-tetrazol-4-yl)thiomethyl]-3-cephem-4-carboxylic acidHCID 178454536(6R,7R)-3-[(1-aminotetrazol-5-yl)sulfanylmethyl]-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-butoxyiminoacetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

Product 1

HCID 16162312HCID 16162312, compoundYield 41.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 31374DimethylacetamideSolvent2×

Procedure

A solution of 2-(2-tritylaminothiazol-4-yl)-(Z)-2-trityloxyiminoacetic acid (4.7 g, 7 mmol) (cf. Tetrahedron 1978, 34, 2233), 1-hydroxybenzotriazole (1.04 g, 7.7 mmol) and N,N'-dicyclohexylcarbodiimide (1.51 g, 7.35 mmol) in dimethylacetamide (27 ml) was allowed to react at room temperature for an hour. To the solution was added a solution of 7β-amino-3-[(1-amino-1H-tetrazol-4-yl)thiomethyl]-3-cephem-4-carboxylic acid (2.54 g, 7.7 mmol) and triethylamine (1.56 g, 15.4 mmol) in dimethylacetamide (20 ml) and water (0.5 ml) and the mixture was allowed to react at 5° C. for 1.5 hours. Then the mixture was treated in a manner similar to that described in Example 6, (c) to give pale yellow powder of 7β-[2-(2-tritylaminothiazol-4-yl)-(Z)-2-trityloxyiminoacetamido]-3-[(1-amino-1H-tetrazol-5-yl)thiomethyl]-3-cephem-4-carboxylic acid (2.86 g, 41.6%).

Workup

  1. customto react at room temperature for an hour
  2. customto react at 5° C. for 1.5 hours
  3. additionThen the mixture was treated in a manner similar to

Sources & evidence

ORD record
ord-9e1af00b0cbf41d18cfa21b514d5e9c1
Source dataset
uspto-grants-1986_03
Patent number
US04576938

Reaction notes

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