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2-Tetralone → 2-(s)-(1,2,3,4-Tetrahydro-naphthalen-2-ylamino)-pentanoic acid [5-(5-methoxy-1,5-dimethyl-hexyl)-thiazol-2-yl]-amide

HRID 131653
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HRID 131653 반응식
Cl.[CH3:2][O:3][C:4]([CH3:24])([CH3:23])[CH2:5][CH2:6][CH2:7][CH:8]([C:10]1[S:14][C:13]([NH:15][C:16](=[O:22])[C@@H:17]([NH2:21])[CH2:18][CH2:19][CH3:20])=[N:12][CH:11]=1)[CH3:9].[CH2:25]1[C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[CH2:28][CH2:27][C:26]1=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClC(Cl)C>[CH3:2][O:3][C:4]([CH3:24])([CH3:23])[CH2:5][CH2:6][CH2:7][CH:8]([C:10]1[S:14][C:13]([NH:15][C:16](=[O:22])[C@@H:17]([NH:21][CH:31]2[CH2:32][CH2:33][C:34]3[C:29](=[CH:28][CH:27]=[CH:26][CH:25]=3)[CH2:30]2)[CH2:18][CH2:19][CH3:20])=[N:12][CH:11]=1)[CH3:9].[OH:3][C:4]([CH3:24])([CH3:23])[CH2:5][CH2:6][CH2:7][CH:8]([C:10]1[S:14][C:13]([NH:15][C:16](=[O:22])[C@@H:17]([NH:21][CH:31]2[CH2:32][CH2:33][C:34]3[C:29](=[CH:28][CH:27]=[CH:26][CH:25]=3)[CH2:30]2)[CH2:18][CH2:19][CH3:20])=[N:12][CH:11]=1)[CH3:9]
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참가 물질

6

반응물 3

HCID 682662-TetraloneHCID 5049666Sodium triacetoxyborohydrideHCID 1317269182-(S)-amino-pentanoic acid [5-(5-methoxy-1,5-dimethyl-hexyl)-thiazol-2-yl]-amide HCl salt

생성물 2

HCID 117055192-(s)-(1,2,3,4-Tetrahydro-naphthalen-2-ylamino)-pentanoic acid [5-(5-methoxy-1,5-dimethyl-hexyl)-thiazol-2-yl]-amide
HCID 11712247
2-(s)-(1,2,3,4-Tetrahydro-naphthalen-2-ylamino)-pentanoic acid [5-(5-hydroxy-1,5-dimethyl-hexyl)-thiazol-2-yl]-amide

시약·촉매·용매 1

HCID 63651,1-Dichloroethane용매

실험 절차

A mixture of 2-(S)-amino-pentanoic acid [5-(5-methoxy-1,5-dimethyl-hexyl)-thiazol-2-yl]-amide HCl salt (600 mg, 1.59 mmol) and 2-tetralone (253 mg, 2.07 mmol) in dichloroethane was stirred at room temperature overnight. Sodium triacetoxyborohydride (530 mg, 2.5 mmol) was added and the mixture was stirred at room temperature overnight. The mixture was quenched with water, adjusted pH to around 10 and extracted with methylene chloride. The organic layer was concentrated to dryness. The residue was purified by SCX column after eluting with 1 M NH3/methanol and concentrated to dryness to give 620 mg that was purified by Shimadzu HPLC to give 2-(S)-(1,2,3,4-tetrahydro-naphthalen-2-ylamino)-pentanoic acid [5-(5-methoxy-1,5-dimethyl-hexyl)-thiazol-2-yl]-amide, LC-MS RT=2.2 min, M+1=472.5 as an oil and 2-(S)-(1,2,3,4-tetrahydro-naphthalen-2-ylamino)-pentanoic acid [5-(5-hydroxy-1,5-dimethyl-hexyl)-thiazol-2-yl]-amide, retention time, LC-MS RT=1.9 min, M+1=458.4 as a beige glass form.

후처리

  1. stirringthe mixture was stirred at room temperature overnight
  2. customThe mixture was quenched with water
  3. extractionextracted with methylene chloride
  4. concentrationThe organic layer was concentrated to dryness
  5. customThe residue was purified by SCX column
  6. washafter eluting with 1 M NH3/methanol
  7. concentrationconcentrated to dryness
  8. customto give 620 mg that
  9. customwas purified by Shimadzu HPLC

출처 및 근거

ORD 기록
ord-a1b977cb52b647f28a1188fb5c56bd23
출처 데이터셋
uspto-grants-2008_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07384968B2

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