Triphenylphosphine → HCID 10993240, 화합물

HRID 1603301노트

반응식

HRID 1603301 반응식
CCOC(/N=N/C(OCC)=O)=O.[F:13][C@H:14]([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[CH2:15][OH:16].[F:23][C:24]1[C:29]([F:30])=[C:28]([CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])[CH:27]=[CH:26][C:25]=1[C:36]1[N:41]=[CH:40][C:39](O)=[CH:38][N:37]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1>[F:23][C:24]1[C:29]([F:30])=[C:28]([CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])[CH:27]=[CH:26][C:25]=1[C:36]1[N:37]=[CH:38][C:39]([O:16][CH2:15][C@H:14]([F:13])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])=[CH:40][N:41]=1

참가 물질

6

반응물 4

HCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 10855629(R)-(+)-2-fluorooctanolHCID 196090982-(2,3-Difluoro-4-pentylphenyl)-5-pyrimidinol

생성물 1

HCID 10993240HCID 10993240, 화합물수율 55.3%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

--DEAD (470 mg, 2.70 mmol) in THF (3 ml) was added dropwise via syringe to a stirring solution of (R)-(+)-2-fluorooctanol (396 mg, 2.70 mmol), the hydroxypyrimidine 33 (750 mg, 2.70 mmol) and triphenylphosphine (707 mg, 2.70 mmol) in THF (10 ml) under nitrogen at ambient temperature for 15 h. The solvent was removed in vacuo and the residue was purified by flash chromatography (3 to 5% ethyl acetate-light petroleum) to give the 2-fluorooctyloxypyrimidine 34 (610 mg, 55%) (from MeOH), m.p. 74.7° C.; [α]D25 -3.6° (c 2.7 in CHCl3); νmax /cm-1 (KBr) 2950, 2920, 1575, 1545, 1460, 1440, 1280, 1210, 1130, 1080 and 995; δ 0.90 (6H, overlapping t, Me), 1.26-1.93 (16H, m), 2.70 (2H, t, ArCH2), 4.22 (2H, dd, 3JHF 22 and Jvic 4, OCH2), 4.87 (1H, d of sext, 2JHF 49 and J4, CHF), 7.02 (1H ddd, J7.5, 7 and 2, 5'-H), 7.6 (1H, ddd, J7.5, 7 and 2, 6'-H) and 8.55 (2H, s, 4- and 6-H); m/z 408 (M+), 365, 351, 291, 278, 250 and 221.

후처리

  1. customThe solvent was removed in vacuo
  2. customthe residue was purified by flash chromatography (3 to 5% ethyl acetate-light petroleum)

출처 및 근거

ORD 기록
ord-7315e597595e45e89620c149389a41ea
출처 데이터셋
uspto-grants-1999_11
특허 번호
US05986096

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