Sodium Hydroxide → HCID 58778919, 화합물

HRID 1372612노트

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HRID 1372612 반응식
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9]1[O:10][C:11]2[CH:17]=[C:16]([CH2:18][C:19]([N:21]3[CH2:25][CH2:24][CH2:23][C@H:22]3[CH2:26][O:27][CH:28]3[CH2:33][CH2:32][CH:31]([C:34]([O:36]C)=[O:35])[CH2:30][CH2:29]3)=[O:20])[CH:15]=[CH:14][C:12]=2[N:13]=1.[OH-].[Na+]>C1COCC1.CO>[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9]1[O:10][C:11]2[CH:17]=[C:16]([CH2:18][C:19]([N:21]3[CH2:25][CH2:24][CH2:23][C@H:22]3[CH2:26][O:27][CH:28]3[CH2:29][CH2:30][CH:31]([C:34]([OH:36])=[O:35])[CH2:32][CH2:33]3)=[O:20])[CH:15]=[CH:14][C:12]=2[N:13]=1

참가 물질

5

반응물 2

HCID 14798Sodium HydroxideHCID 58778867HCID 58778867, 화합물

생성물 1

HCID 58778919HCID 58778919, 화합물

시약·촉매·용매 2

HCID 887Methanol용매HCID 8028Tetrahydrofuran용매

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온도
70 °C

실험 절차

In THF (10 ml) and methanol (5 ml) was dissolved methyl 4-(1-(2-(2-methylphenylamino)-6-benzoxazolylacetyl)-(2S)-pyrrolidinylmethoxy)cyclohexanecarboxylate (580 mg, 1.1 mmol), that is, a mixture of two diastereomers (cis and trans forms). After addition of 1N NaOH (1.5 ml, 1.5 mmol), the mixture was stirred at 70° C. for 24 hours. The residue obtained by distilling off the solvent under reduced pressure, was acidified weakly with 1N HCl. The crystals thus precipitated were collected by filtration under reduced pressure. The resulting crystals were washed with water and dried under reduced pressure, whereby 4-(1-(2-(2-methylphenylamino)-6-benzoxazolylacetyl)-(2S)-pyrrolidinylmethoxy)cyclohexanecarboxylic acid was obtained as a mixture of two diasteromers. The mixture was separated by HPLC (C18 column, eluting with 0.02N acetate buffer-acetonitrile (1:1, v/v)), whereby Isomer A (150 mg, 27%) was obtained as a white crystalline solid.

후처리

  1. additiona mixture of two diastereomers (cis and trans forms)
  2. customThe residue obtained
  3. distillationby distilling off the solvent under reduced pressure
  4. customThe crystals thus precipitated
  5. filtrationwere collected by filtration under reduced pressure
  6. washThe resulting crystals were washed with water
  7. customdried under reduced pressure

출처 및 근거

ORD 기록
ord-72dc8c6047034c94811b32296ab65cfb
출처 데이터셋
uspto-grants-2007_01
특허 번호
US07157487B2

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