Potassium Carbonate → (2R,3R)-2-(7-cyanobenzo[b]thiophen-4-ylamino)-3-hydroxybutanoic acid

HRID 470856

반응식

HRID 470856 반응식
C([O-])([O-])=O.[K+].[K+].F[C:8]1[C:16]2[CH:15]=[CH:14][S:13][C:12]=2[C:11]([C:17]#[N:18])=[CH:10][CH:9]=1.[NH2:19][C@@H:20]([C:24]([OH:26])=[O:25])[C@@H:21]([CH3:23])[OH:22]>CS(C)=O>[C:17]([C:11]1[C:12]2[S:13][CH:14]=[CH:15][C:16]=2[C:8]([NH:19][C@H:20]([C@H:21]([OH:22])[CH3:23])[C:24]([OH:26])=[O:25])=[CH:9][CH:10]=1)#[N:18]

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 90624D-AllothreonineHCID 670062384-Fluoro-1-benzothiophene-7-carbonitrile

생성물 1

HCID 67007071(2R,3R)-2-(7-cyanobenzo[b]thiophen-4-ylamino)-3-hydroxybutanoic acid수율 100%

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

반응 조건

온도
80 °C

실험 절차

K2CO3 (1.50 g, 10.9 mmol) was added to a mixture of 4-fluorobenzo[b]thiophene-7-carbonitrile (770 mg, 4.35 mmol) and D-Allo-threonine (620 mg, 5.20 mmol) in DMSO (10 mL) at room temperature. The resulting mixture was heated to 80° C. and stirred for 15 h. After cooling to room temperature, the reaction mixture was poured into ice-water (150 mL) and extracted with 10% EtOAc in hexanes (2×50 mL). The aqueous phase was acidified to pH=2˜3 with 2N HCl and extracted with EtOAc (2×100 mL). The EtOAc extracts were washed with water, brine and dried with Na2SO4. Removal of the solvent gave the crude (2R,3R)-2-(7-cyanobenzo[b]thiophen-4-ylamino)-3-hydroxybutanoic acid (1.20 g, ˜100%). 1H NMR (400 MHz, Acetone-d6, δ in ppm) 7.81 (d, J=5.7 Hz, 1H), 7.70 (d, J=5.7 Hz, 1H), 7.64 (d, J=8) Hz, 1H), 6.72 (d, J=8.2 Hz, 1H), 6.28 (d, J=8.2 Hz, 1H), 4.33 (m, 2H), 1.39 (d, J=6.4 Hz, 3H).

후처리

  1. temperatureAfter cooling to room temperature
  2. extractionextracted with 10% EtOAc in hexanes (2×50 mL)
  3. extractionextracted with EtOAc (2×100 mL)
  4. washThe EtOAc extracts were washed with water, brine
  5. dry with materialdried with Na2SO4
  6. customRemoval of the solvent

출처 및 근거

ORD 기록
ord-85431e07ae044b53988e6e4a66d53fe6
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08629167B2

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