Hydrochloric Acid → 6-[5-(2-Oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl)pentanoylamino]hexanoic acid

HRID 1616994

반응식

HRID 1616994 반응식
O=C1CCC(=O)N1O[C:9](=[O:23])[CH2:10][CH2:11][CH2:12][CH2:13][CH:14]1[CH:21]2[CH:17]([NH:18][C:19](=[O:22])[NH:20]2)[CH2:16][S:15]1.[NH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][C:30]([OH:32])=[O:31].Cl>CN(C=O)C.C(=O)(O)[O-].[Na+]>[O:22]=[C:19]1[NH:18][CH:17]2[CH2:16][S:15][CH:14]([CH2:13][CH2:12][CH2:11][CH2:10][C:9]([NH:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][C:30]([OH:32])=[O:31])=[O:23])[CH:21]2[NH:20]1

참가 물질

6

반응물 3

HCID 313Hydrochloric AcidHCID 5646-Aminohexanoic AcidHCID 434213NHS-Biotin

생성물 1

HCID 51626646-[5-(2-Oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl)pentanoylamino]hexanoic acid

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 516892Sodium Bicarbonate용매

실험 절차

5-(2-Oxo-hexahydro-thieno[3,4-d]imidazol-4-yl)-pentanoic acid 2,5-dioxo-pyrrolidin-1-yl ester (2; 0.35 g, 1.03 mmol) was completely dissolved in DMF (3 mL) with gentle warming. After cooling the 2 solution to room temperature without reprecipitation, it was mixed with a solution of ε-aminocaproic acid (0.18 g, 1.37 mmol) in sodium bicarbonate buffer (0.1 M, pH 8.0; 4 mL) while stirring. After 4 h at room temperature, the reaction mixture was acidified by HCl solution (1 N) to assist in the formation of white precipitate. The white solid was washed with cold HCl solution, dried over ether, and air-dried to afford 3 (0.30 g; 80.5%). 1H NMR (400 MHz) (DMSO) δ: 7.78 (s, 1H, CONH), 6.46 (s, 1H, CONH), 6.38 (s, 1H, CONH), 4.32 (t, 1H, CHN), 4.14 (t, 1H, CHN), 3.11 (dd, 1H, CHS), 3.02 (t, 2H, CH2NH), 2.84 (d, 1H, CHHS), 2.59 (d, 1H, CHHS), 2.18 (t, 2H, CH2COOH), 2.05 (t, 2H, CH2CO), 1.23-1.68 (m, 12H). 13C NMR (100.67 MHz) (DMSO) δ: 174.45, 171.79, 162.70, 61.03, 59.18, 55.43, 35.21, 33.60, 28.90, 28.02, 25.97, 25.33, 24.22. HRMS (ESI) calculated for C16H27N3O4S, [M+Na]+ 380.1620 (calcd.), 380.1617 (found).

후처리

  1. customwithout reprecipitation, it
  2. washThe white solid was washed with cold HCl solution
  3. dry with materialdried over ether
  4. customair-dried
  5. customto afford 3 (0.30 g; 80.5%)

출처 및 근거

ORD 기록
ord-a909064667bf4a789cb5df16ac5fd2cf
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08765934B2

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