Ammonia → HCID 67661527, compound

HRID 964714Notes

Reaction equation

HRID 964714 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]([CH2:12][C:13]([CH3:16])([CH3:15])[CH3:14])[C:10](=[O:17])[C@@H:9]([CH2:18][C:19]([OH:21])=O)[S:8][C@H:7]([C:22]3[C:31]4[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=4)[CH:25]=[CH:24][CH:23]=3)[C:6]=2[CH:32]=1.C(N1C=CN=C1)([N:35]1C=CN=C1)=O.N>O1CCCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]([CH2:12][C:13]([CH3:16])([CH3:15])[CH3:14])[C:10](=[O:17])[C@@H:9]([CH2:18][C:19]([NH2:35])=[O:21])[S:8][C@H:7]([C:22]3[C:31]4[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=4)[CH:25]=[CH:24][CH:23]=3)[C:6]=2[CH:32]=1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 682631,1'-CarbonyldiimidazoleHCID 11488185HCID 11488185, compound

Product 1

HCID 67661527HCID 67661527, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of trans-7-chloro-5-(naphthalen-1-yl)-1-neopentyl-1,2,3,5-tetrahydro-2-oxo-4,1-benzothiazepine-3-acetic acid (200 mg, 426 μmol), 1,1'-carbonyidiimidazole (143 mg, 853 μmol) and tetrahydrofuran (5 mL) was heated at reflux for 1.5 hours. The resulting reaction mixture was cooled to 0° C. and a solution of tetrahydrofuran saturated with anhydrous ammonia (5 mL) was added. After 0.5 hours the reaction mixture was warmed to ambient temperature, concentrated under reduced pressure and purified by flash column chromatography (1:1 hexanes/ethyl acetate) to provide 200 mg (quantitative) of the title compound as a white powder.

Workup

  1. temperatureat reflux for 1.5 hours
  2. customThe resulting reaction mixture
  3. temperatureAfter 0.5 hours the reaction mixture was warmed to ambient temperature
  4. concentrationconcentrated under reduced pressure
  5. custompurified by flash column chromatography (1:1 hexanes/ethyl acetate)

Sources & evidence

ORD record
ord-58a70ba41dfd451f83333d073c7755a6
Source dataset
uspto-grants-1998_06
Patent number
US05770594

Reaction notes

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