Triethylamine → {(S)-1-[(R)-1-(3-Amino-1-cyclopropyl-6-fluoro-2,4-dioxo-1,2,3,4-tetrahydropyrido[2,3-d]pyrimidin-7-yl)pyrrolidin-3-yl]ethyl}-carbamic acid tert-butyl ester

HRID 10337

반응식

HRID 10337 반응식
[NH2:1][N:2]1[C:7](=[O:8])[C:6]2[CH:9]=[C:10]([F:17])[C:11](S(=S)(O)=O)=[N:12][C:5]=2[N:4]([CH:18]2[CH2:20][CH2:19]2)[C:3]1=[O:21].[C:22]([O:26][C:27](=[O:36])[NH:28][C@@H:29]([C@H:31]1[CH2:35][CH2:34][NH:33][CH2:32]1)[CH3:30])([CH3:25])([CH3:24])[CH3:23].C(N(CC)CC)C>C(#N)C>[C:22]([O:26][C:27](=[O:36])[NH:28][C@H:29]([C@@H:31]1[CH2:35][CH2:34][N:33]([C:11]2[C:10]([F:17])=[CH:9][C:6]3[C:7](=[O:8])[N:2]([NH2:1])[C:3](=[O:21])[N:4]([CH:18]4[CH2:20][CH2:19]4)[C:5]=3[N:12]=2)[CH2:32]1)[CH3:30])([CH3:23])([CH3:24])[CH3:25]

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 10104699(3S,1R)-3-(1-(t-butoxycarbonylamino)ethyl)pyrrolidineHCID 219790013-Amino-1-cyclopropyl-6-fluoro-2,4-dioxo-1,2,3,4-tetrahydro-pyrido[2,3-d]pyrimidine-7-thiosulfonic acid2회

생성물 1

HCID 58681891{(S)-1-[(R)-1-(3-Amino-1-cyclopropyl-6-fluoro-2,4-dioxo-1,2,3,4-tetrahydropyrido[2,3-d]pyrimidin-7-yl)pyrrolidin-3-yl]ethyl}-carbamic acid tert-butyl ester수율 58.7%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

A solution of 0.12 g (0.38 mmol) of 3-amino-1-cyclopropyl-6-fluoro-2,4-dioxo-1,2,3,4-tetrahydro-pyrido[2,3-d]pyrimidine-7-thiosulfonic acid (Compound 24c) in 10 mL of acetonitrile is treated with 0.24 g (1.14 mmol) of ((R)-(S)-1-pyrrolidin-3-ylethyl)carbamic acid tert-butyl ester (J. Het. Chem., 1992; 29:1481), 0.25 g (2.5 mmol) of triethylamine and stirred at room temperature for 18 hours then 50° C. for 1 hour. The solvent is removed in vacuo and the residue is partitioned between ethyl acetate (50 mL) and water (25 mL). The organic layer is washed with water, dried (MgSO4), filtered and evaporated in vacuo to give 0.28 g. Chromatography on flash grade silica gel (230–400 mesh) column (2×12 cm) eluting with dichloromethane/ethanol (95:5) provided 0.1 g of the title compound, mp 175–177° C.

후처리

  1. wait50° C. for 1 hour
  2. customThe solvent is removed in vacuo
  3. customthe residue is partitioned between ethyl acetate (50 mL) and water (25 mL)
  4. washThe organic layer is washed with water
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customevaporated in vacuo
  8. customto give 0.28 g
  9. washChromatography on flash grade silica gel (230–400 mesh) column (2×12 cm) eluting with dichloromethane/ethanol (95:5)

출처 및 근거

ORD 기록
ord-7617c6a9714f4fc1badb4dccedb07ffc
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07094780B1

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