Dicyclohexylcarbodiimide → HCID 46840422, 화합물

HRID 469452노트

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HRID 469452 반응식
[CH3:1][O:2][C:3]([C:5]1[S:6][CH:7]=[CH:8][C:9]=1[NH:10][CH:11]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:12]([OH:14])=[O:13])=[O:4].[N:21]12[CH2:28][CH2:27][CH:24]([CH2:25][CH2:26]1)[C@@H:23](O)[CH2:22]2.C1CCC(N=C=NC2CCCCC2)CC1.C1C=CC2N(O)N=NC=2C=1>C1COCC1>[O:13]=[C:12]([O:14][C@@H:23]1[CH:24]2[CH2:27][CH2:28][N:21]([CH2:26][CH2:25]2)[CH2:22]1)[CH:11]([NH:10][C:9]1[CH:8]=[CH:7][S:6][C:5]=1[C:3]([O:2][CH3:1])=[O:4])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

참가 물질

6

반응물 4

HCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 914043-Quinuclidinol, (-)-HCID 58557000HCID 58557000, 화합물

생성물 1

HCID 46840422HCID 46840422, 화합물수율 28%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

A mixture of 2-(2-(methoxycarbonyl)thiophen-3-ylamino)-2-phenylacetic acid (I10) (404 mg, 1.39 mmol), (R)-quinuclidin-3-ol (529 mg, 4.17 mmol), DCC (859 mg, 4.17 mmol) and HOBT (567 mg, 4.17 mmol) in dry THF (25 ml) was stirred at room temperature overnight. THF was evaporated, and the crude product was taken up with EtOAc and washed twice with 2M K2CO3. The organic phase was dried over Na2SO4, filtered and evaporated to dryness. The crude was purified by flash chromatography (DCM/MeOH=98/2 to 95/5) recovering diastereomer 1 of C11 (161 mg; 28% yield), and subsequently diastereomer 2 of C11 (127 g, 35% yield).

후처리

  1. customTHF was evaporated
  2. washwashed twice with 2M K2CO3
  3. dry with materialThe organic phase was dried over Na2SO4
  4. filtrationfiltered
  5. customevaporated to dryness
  6. customThe crude was purified by flash chromatography (DCM/MeOH=98/2 to 95/5)
  7. customrecovering diastereomer 1 of C11 (161 mg; 28% yield), and subsequently diastereomer 2 of C11 (127 g, 35% yield)

출처 및 근거

ORD 기록
ord-d6c56ec0ffe94cd9a15280369967b156
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08629160B2

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