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

反応式

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

参加物

反応物 3

HCID 6422Trifluoroacetic acid

HCID 2724699PyBOP

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

生成物 1

HCID 38042593-Hydroxyisobenzofuran-1(3H)-one収率 35%

実験手順

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)+.

後処理

custompurified by reverse phase HPLC

出典と根拠

ORDレコード: ord-3dd122e0e62e4fd8b272ad0670402c45
出典データセット: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
特許番号: US07592331B2

反応ノート

読み込み中…