Hydrochloric Acid → 2-{3-[2-(4-Trifluoromethyl-phenyl)-ethoxycarbonylmethyl]phenylsulfanylmethyl}-benzoic acid 2,2,2-trichloro-ethyl ester

HRID 709489

반응식

HRID 709489 반응식
[Cl:1][C:2]([Cl:37])([Cl:36])[CH2:3][O:4][C:5](=[O:35])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[CH2:12][S:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([CH2:20][C:21]([O:23]CC2C=CC(C(F)(F)F)=CC=2)=[O:22])[CH:15]=1.ClC(Cl)(Cl)COC(=O)C1C=CC=CC=1CSC1C=CC=C(CC(O)=O)C=1.[F:64][C:65]([F:76])([F:75])[C:66]1[CH:71]=[CH:70][C:69]([CH:72](O)[CH3:73])=[CH:68][CH:67]=1.Cl>CN(C1C=CN=CC=1)C.CCCCCCC.CCOC(C)=O.C(Cl)Cl.C(Cl)CCl>[Cl:1][C:2]([Cl:36])([Cl:37])[CH2:3][O:4][C:5](=[O:35])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[CH2:12][S:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([CH2:20][C:21]([O:23][CH2:73][CH2:72][C:69]2[CH:68]=[CH:67][C:66]([C:65]([F:64])([F:75])[F:76])=[CH:71][CH:70]=2)=[O:22])[CH:15]=1

참가 물질

10

반응물 4

HCID 313Hydrochloric AcidHCID 1371861-[4-(Trifluoromethyl)phenyl]ethan-1-olHCID 668648212-(3-Carboxymethyl-phenylsulfanylmethyl)-benzoic acid 2,2,2-trichloro-ethyl esterHCID 866503082-[3-(4-Trifluoromethyl-benzyloxycarbonylmethyl)-phenylsulfanylmethyl]-benzoic acid 2,2,2-trichloro-ethyl ester

생성물 1

HCID 866503122-{3-[2-(4-Trifluoromethyl-phenyl)-ethoxycarbonylmethyl]phenylsulfanylmethyl}-benzoic acid 2,2,2-trichloro-ethyl ester수율 68%

시약·촉매·용매 5

HCID 142844-(Dimethylamino)pyridine촉매HCID 111,2-Dichloroethane용매HCID 6344Dichloromethane용매HCID 8857Ethyl Acetate용매HCID 8900Heptane용매

실험 절차

The titled compound was prepared according to the method described for 2-[3-(4-trifluoromethyl-benzyloxycarbonylmethyl)-phenylsulfanylmethyl]-benzoic acid 2,2,2-trichloro-ethyl ester above from 2-(3-carboxymethyl-phenylsulfanylmethyl)-benzoic acid 2,2,2-trichloro-ethyl ester (168 mg, 0.387 mmol), 1-(4-trifluoromethyl-phenyl)-ethanol (88 mg, 0.465 mmol), EDC×HCl (111 mg, 0.581 mmol), DMAP (4.7 mg, 0.039 mmol) and DCM (4 mL). The crude was submitted to flash chromatography using heptane and EtOAc (90/10) as eluent to yield the titled compound (160 mg, 68%) as an oil; 1H NMR (400 MHz, CDCl3): δ 2.67 (dd, 2H), 3.23 (s, 2H), 4.03 (dd, 2H), 4.27 (s, 2H), 4.67 (s, 2H), 6.74 (br d, 1H), 6.85-6.99 (m, 6H), 7.06 (dd, 1H), 7.13 (dd, 1H), 7.22 (d, 2H), 7.79 (d, 1H); Mass spectrum: M−H+ 604.

후처리

  1. customThe titled compound was prepared

출처 및 근거

ORD 기록
ord-6b2b1ab8453b4f2994c49a6560786302
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09181181B2

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