Trifluoroacetic acid → 3-Hydroxyisobenzofuran-1(3H)-one

HRID 735586노트

반응식

HRID 735586 반응식
NCC1C=C(NC([O:17][CH2:18][CH2:19][C:20]2C=C[C:23](C(NC3C=C4C(=CC=3)C(N(C(OC(C)(C)C)=O)C(OC(C)(C)C)=O)=NC=C4)C(O)=O)=[CH:22][C:21]=2C)=O)C=CC=1S(CC)(=O)=O.C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.[C:90]([OH:96])([C:92](F)(F)F)=[O:91]>>[OH:91][CH:90]1[C:92]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[C:18](=[O:17])[O:96]1

참가 물질

4

반응물 3

HCID 6422Trifluoroacetic acidHCID 2724699PyBOPHCID 578427962-(4-(2-(3-(Aminomethyl)-4-(ethylsulfonyl)phenylcarbamoyloxy)ethyl)-3-methylphenyl)-2-(1-(bis(tert-butoxycarbonyl)amino)isoquinolin-6-ylamino)acetic acid

생성물 1

HCID 38042593-Hydroxyisobenzofuran-1(3H)-one수율 35%

실험 절차

Using a procedure analogous to that used to prepare Example 28, 31D (400 mg, 0.51 mmol) was cyclized with PyBOP instead of BOP, deprotected with TFA, and purified by reverse phase HPLC to give Example 31 (100 mg, 35%) as a tan solid. 1H NMR (400 MHz, CD3OD) δ ppm 1.09-1.24 (m, 3 H) 2.27 (s, 2 H) 2.49 (s, 2 H) 2.67-2.88 (m, 1 H) 3.05-3.17 (m, 1 H) 3.22-3.28 (m, 2 H) 4.05 (d, J=9.89 Hz, 0.5 H) 4.13-4.25 (m, 0.5 H) 4.29-4.39 (m, 1 H) 5.01-5.12 (m, 2 H) 5.14-5.18 (m, J=3.30 Hz, 1 H) 6.43 (none, 1 H) 6.68 (d, J=2.75 Hz, 1 H) 6.70-6.78 (m, J=5.50 Hz, 1 H) 6.78-6.86 (m, 1 H) 6.92-7.16 (m, 2.5 H) 7.21 (m, 0.5 H) 7.44 (m, 0.5 H) 7.51 (s, 0.5 H) 7.65-7.74 (m, 1 H) 7.90-8.02 (m, 1 H) 8.76-8.92 (m, J=6.05 Hz, 1 H). MS (ESI) m/z 574.18 (M+H)+.

후처리

  1. custompurified by reverse phase HPLC

출처 및 근거

ORD 기록
ord-3dd122e0e62e4fd8b272ad0670402c45
출처 데이터셋
uspto-grants-2009_09
특허 번호
US07592331B2

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