Diisopropylethylamine → HCID 11674493, 화합물

HRID 1866117노트

반응식

HRID 1866117 반응식
[C:1]1([C@H:7]([CH2:11][CH3:12])[C:8]([OH:10])=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(C(C)C)CC)(C)C.F[P-](F)(F)(F)(F)F.N1(O[P+](N2CCCC2)(N2CCCC2)N2CCCC2)C2C=CC=CC=2N=N1.[F:55][C:56]1[CH:61]=[CH:60][C:59]([C:62]([F:65])([F:64])[F:63])=[CH:58][C:57]=1[CH2:66][NH2:67]>CN(C)C=O>[F:55][C:56]1[CH:61]=[CH:60][C:59]([C:62]([F:63])([F:64])[F:65])=[CH:58][C:57]=1[CH2:66][NH:67][C:8](=[O:10])[C@H:7]([C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)[CH2:11][CH3:12]

참가 물질

6

반응물 4

HCID 81531DiisopropylethylamineHCID 5338392-Fluoro-5-(trifluoromethyl)benzylamineHCID 785329(S)-2-Phenylbutyric acidHCID 2724699PyBOP

생성물 1

HCID 11674493HCID 11674493, 화합물

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

A solution of (S)-2-phenylbutanoic acid (1-d, 50 mg, 0.30 mmol, Sigma-Aldrich, Milwaukee, Wis.) and diisopropylethylamine (98 uL, 0.60 mmol) in N,N-dimethylformamide (1 mL) was treated at room temperature with benzotriazol-1-yloxytripyrrolidinophosphonium hexafluorophosphate (PyBop, 158 mg, 0.30 mmol). After 15 min, (2-fluoro-5-(trifluoromethyl)phenyl)methanamine (1-g, 60 mg, 0.30 mmol, Synthesis, Inc., Wyndham, N.H.) was added. The reaction mixture was stirred for 3 h, partitioned between dichioromethane and 0.5N—NaOH. The aqueous layer was removed and the organic layer was washed with 0.5N—HCl. The aqueous layer was removed by filtering through a plastic frit. The organic layer was concentrated in vacuo to give the desired product (1-1); HRMS (M+1)=340.129; 1H NMR (500 MHz, CDCl3) δ7.49 (bs, 1H), 7.41 (d, 1H, J=6.5 Hz), 7.34-7.26 (m, 5H), 7.10 (t, 1H, J=9.0 Hz), 5.77 (bs, 1H), 4.47 (d, 1H, J=3.0 Hz), 3.30 (t, 2H, J=7.5 Hz), 2.22 (m, 1H), 1.82 (m, 1H), 0.89 (t, 3H, J=7.5 Hz).

후처리

  1. custompartitioned between dichioromethane and 0.5N—NaOH
  2. customThe aqueous layer was removed
  3. washthe organic layer was washed with 0.5N—HCl
  4. customThe aqueous layer was removed
  5. filtrationby filtering through a plastic frit
  6. concentrationThe organic layer was concentrated in vacuo

출처 및 근거

ORD 기록
ord-2f9658b55f0e4702ba1aac3a0b46e453
출처 데이터셋
uspto-grants-2009_12
특허 번호
US07629367B2

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