Dicyclohexylcarbodiimide → benzyl 3-{[(3R)-4-benzoyl-8-(4-isopropylphenoxy)-1-thia-4-azaspiro[4.5]decan-3-yl]carbonyl}amino-propionate

HRID 1934747노트

반응식

HRID 1934747 반응식
[C:1]([N:9]1[C:13]2([CH2:18][CH2:17][CH:16]([O:19][C:20]3[CH:25]=[CH:24][C:23]([CH:26]([CH3:28])[CH3:27])=[CH:22][CH:21]=3)[CH2:15][CH2:14]2)[S:12][CH2:11][C@H:10]1[C:29](O)=[O:30])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:32][CH2:33][CH2:34][C:35]([O:37][CH2:38][C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)=[O:36].O.ON1C2C=CC=CC=2N=N1.C1(N=C=NC2CCCCC2)CCCCC1>O1CCCC1>[C:1]([N:9]1[C:13]2([CH2:18][CH2:17][CH:16]([O:19][C:20]3[CH:25]=[CH:24][C:23]([CH:26]([CH3:28])[CH3:27])=[CH:22][CH:21]=3)[CH2:15][CH2:14]2)[S:12][CH2:11][C@H:10]1[C:29]([NH:32][CH2:33][CH2:34][C:35]([O:37][CH2:38][C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)=[O:36])=[O:30])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

6

반응물 4

HCID 10868DicyclohexylcarbodiimideHCID 1116164Benzyl 3-aminopropanoateHCID 27960291-Hydroxybenzotriazole hydrateHCID 70154971(3R)-4-benzoyl-8-(4-isopropylphenoxy)-1-thia-4-azaspiro[4.5]decane-3-carboxylic acid

생성물 1

HCID 70156809benzyl 3-{[(3R)-4-benzoyl-8-(4-isopropylphenoxy)-1-thia-4-azaspiro[4.5]decan-3-yl]carbonyl}amino-propionate수율 80.5%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

In 10 ml of anhydrous tetrahydrofuran was dissolved 0.50 g of (3R)-4-benzoyl-8-(4-isopropylphenoxy)-1-thia-4-azaspiro[4.5]decane-3-carboxylic acid. Then, at 0-5° C., 0.22 g of benzyl 3-aminopropionate, 0.19 g of 1-hydroxybenzotriazole monohydrate and 0.26 g of dicyclohexyl carbodiimide were added successively. After stirring the resulting mixture at the same temperature as above for 30 minutes and then at ambient temperature for 5 hours, the insoluble matter was filtered off. The filtrate was poured into a mixture of water and ethyl acetate, pH was adjusted to 2.0 with 2 mol/L hydrochloric acid, and the organic layer was separated. The organic layer thus obtained was washed successively with water, saturated aqueous solution of sodium hydrogen carbonate and saturated aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. Purification of the residue by column chromatography [eluent: hexane:ethyl acetate=2:1] gave 0.55 g of benzyl 3-{[(3R)-4-benzoyl-8-(4-isopropylphenoxy)-1-thia-4-azaspiro[4.5]decan-3-yl]carbonyl}amino-propionate as a colorless oily product.

후처리

  1. waitat ambient temperature for 5 hours
  2. filtrationthe insoluble matter was filtered off
  3. additionThe filtrate was poured into a mixture of water and ethyl acetate, pH
  4. customthe organic layer was separated
  5. customThe organic layer thus obtained
  6. washwas washed successively with water, saturated aqueous solution of sodium hydrogen carbonate and saturated aqueous solution of sodium chloride
  7. dry with materialdried over anhydrous magnesium sulfate
  8. distillationthe solvent was distilled off under reduced pressure
  9. customPurification of the residue by column chromatography [eluent: hexane:ethyl acetate=2:1]

출처 및 근거

ORD 기록
ord-46b67dfd94a043c49500f76d05fb8614
출처 데이터셋
uspto-grants-2002_05
특허 번호
US06384065B1

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