Lithium Hydroxide → 2-(6,8-Difluoro-1,2,3,4-tetrahydro-naphthalen-2-ylamino)-pentanoic acid

HRID 505044

반응식

HRID 505044 반응식
C[O:2][C:3](=[O:21])[CH:4]([NH:8][CH:9]1[CH2:18][CH2:17][C:16]2[C:11](=[C:12]([F:20])[CH:13]=[C:14]([F:19])[CH:15]=2)[CH2:10]1)[CH2:5][CH2:6][CH3:7].[Li+].[OH-]>C1COCC1.O>[F:19][C:14]1[CH:15]=[C:16]2[C:11](=[C:12]([F:20])[CH:13]=1)[CH2:10][CH:9]([NH:8][CH:4]([CH2:5][CH2:6][CH3:7])[C:3]([OH:21])=[O:2])[CH2:18][CH2:17]2

참가 물질

4

반응물 2

HCID 3939Lithium HydroxideHCID 671643272-(6,8-Difluoro-1,2,3,4-tetrahydro-naphthalen-2-ylamino)-pentanoic acid methyl ester

생성물 1

HCID 211128022-(6,8-Difluoro-1,2,3,4-tetrahydro-naphthalen-2-ylamino)-pentanoic acid

시약·촉매·용매 1

HCID 21881883Oxolane--water (1/1)용매

실험 절차

2-(6,8-Difluoro-1,2,3,4-tetrahydro-naphthalen-2-ylamino)-pentanoic acid methyl ester (1 equiv) is dissolved in THF:water (5:1) and LiOH (1.2 equiv) is added. The reaction is stirred overnight at rt, the solvent is removed, water added, and the pH is adjusted to 7 using 1N hydrochloric acid. The solid is filtered, washed with water and diethyl ether, and dried to afford 2-(6,8-Difluoro-1,2,3,4-tetrahydro-naphthalen-2-ylamino)-pentanoic acid; Acid derived from diasteromer 1: H1 NMR (400 MHz, CD3OD) 0.99 (t, 3H, J=7.5), 1.48 (m, 2H), 1.82 (m, 3H), 2.36 (m, 1H), 2.65 (m, 1H), 2.95 (m, 2H), 3.28 (s, 1H), 3.42 (m, 1H), 3.74 (m, 1H), 6.80 (m, 2H); (MS m/z 284.3 (M+1). Acid derived from diasteromer 2: H1 NMR (400 MHz, CD3OD) 0.94 (t, 3H, J=7.6), 1.42 (m, 2H), 1.56 (m, 3H), 1.96 (m, 1H), 2.25 (m, 1H), 2.85 (m, 3H), 3.15 (m, 1H), 3.25 (m, 1H), 6.64 (m, 2H); MS m/z 284.2 (M+1).

후처리

  1. customthe solvent is removed
  2. additionwater added
  3. filtrationThe solid is filtered
  4. washwashed with water and diethyl ether
  5. customdried

출처 및 근거

ORD 기록
ord-e7070b8a995a4559b39ac3aa1900fa4b
출처 데이터셋
uspto-grants-2010_08
특허 번호
US07781435B2

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