Water → trans-(R)-3-(4-(((4-tert-butylcyclohexyl)(1-methyl-1H-benzo[d]imidazol-2-yl)amino)methyl)benzamido)-2-hydroxypropanoic acid

HRID 229991노트

반응식

HRID 229991 반응식
[C:1]([CH:5]1[CH2:10][CH2:9][CH:8]([N:11]([CH2:22][C:23]2[CH:38]=[CH:37][C:26]([C:27]([NH:29][CH2:30][C@@H:31]([OH:36])[C:32]([O:34]C)=[O:33])=[O:28])=[CH:25][CH:24]=2)[C:12]2[N:16]([CH3:17])[C:15]3[CH:18]=[CH:19][CH:20]=[CH:21][C:14]=3[N:13]=2)[CH2:7][CH2:6]1)([CH3:4])([CH3:3])[CH3:2].[Li+].[OH-].O>CO>[C:1]([CH:5]1[CH2:10][CH2:9][CH:8]([N:11]([CH2:22][C:23]2[CH:24]=[CH:25][C:26]([C:27]([NH:29][CH2:30][C@@H:31]([OH:36])[C:32]([OH:34])=[O:33])=[O:28])=[CH:37][CH:38]=2)[C:12]2[N:16]([CH3:17])[C:15]3[CH:18]=[CH:19][CH:20]=[CH:21][C:14]=3[N:13]=2)[CH2:7][CH2:6]1)([CH3:4])([CH3:2])[CH3:3]

참가 물질

5

반응물 3

HCID 962WaterHCID 3939Lithium Hydroxide2회HCID 57758784Methyl (2r)-3-[(4-{[(4-tert-butylcyclohexyl)(1-methyl-1h-benzimidazol-2-yl)amino]-methyl}benzoyl)amino]-2-hydroxypropanoate

생성물 1

HCID 44561584trans-(R)-3-(4-(((4-tert-butylcyclohexyl)(1-methyl-1H-benzo[d]imidazol-2-yl)amino)methyl)benzamido)-2-hydroxypropanoic acid

시약·촉매·용매 1

HCID 887Methanol용매

반응 조건

온도
40 °C

실험 절차

To a solution of the title compound of Example 7 (0.1 mmol, 50 mg) in 2 mL of MeOH was added LiOH (0.5 mmol, 12 mg). H2O was added dropwise until the reaction became slightly cloudy, then the mixture was sonicated to dissolve the LiOH. The reaction was stirred at 40° C. for 2 h. The reaction was concentrated under reduced pressure and the residue was taken up in dioxane/H2O and acidified with TFA. Purification by reverse-phase HPLC (Condition A), followed by lyophilization, afforded the title compound as a white solid. 1H NMR (500 MHz, CD3OD): δ 7.79 (d, 2H), 7.58 (m, 1H), 7.39-7.52 (overlapping m, 5H), 4.86 (s, 2H), 4.34 (m, 1H), 3.87 (s, 3H), 3.52-3.84 (overlapping m, 3H), 2.16 (m, 2H), 1.99 (m, 2H), 1.84 (m, 2H), 1.31 (m, 2H), 1.14 (m, 1H), 0.92 (s, 9H). MS (ESI): m/z 487 (M+H). MS (ESI): m/z 507 (M+H). HPLC A: 1.84 min.

후처리

  1. customthe mixture was sonicated
  2. concentrationThe reaction was concentrated under reduced pressure
  3. customPurification by reverse-phase HPLC (Condition A),

출처 및 근거

ORD 기록
ord-897a23569364414a96b2ee13a0139ec2
출처 데이터셋
uspto-grants-2009_07
특허 번호
US07563815B2

반응 노트

불러오는 중…