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

HRID 1616994

反応式

HRID 1616994 の反応式
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

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 516892Sodium Bicarbonate溶媒

実験手順

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).

後処理

  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%)

出典と根拠

ORDレコード
ord-a909064667bf4a789cb5df16ac5fd2cf
出典データセット
uspto-grants-2014_07
特許番号
US08765934B2

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