Water → HCID 15020966、化合物

HRID 278631ノート

反応式

HRID 278631 の反応式
C(=O)([O-])OC1C=CC([N+]([O-])=O)=CC=1[CH2:12][CH:13]1[C:25]2[C:20](=[C:21]3[CH:33]=[CH:32][CH:31]=[CH:30][C:22]3=[C:23]3[CH:29]=[CH:28][CH:27]=[CH:26][C:24]3=2)[C:19]2[C:14]1=[C:15]1[CH:41]=[CH:40][CH:39]=[CH:38][C:16]1=[C:17]1[CH:37]=[CH:36][CH:35]=[CH:34][C:18]1=2.[C:44]([OH:47])(=[O:46])C.[C:48]([O:52][C:53](=[O:56])[CH2:54][NH2:55])([CH3:51])([CH3:50])[CH3:49].O.OS([O-])(=O)=O.[K+]>ClCCl>[C:48]([O:52][C:53](=[O:56])[CH2:54][NH:55][C:44]([O:47][CH2:12][CH:13]1[C:14]2[C:19](=[C:18]3[CH:34]=[CH:35][CH:36]=[CH:37][C:17]3=[C:16]3[CH:38]=[CH:39][CH:40]=[CH:41][C:15]3=2)[C:20]2[C:25]1=[C:24]1[CH:26]=[CH:27][CH:28]=[CH:29][C:23]1=[C:22]1[CH:30]=[CH:31][CH:32]=[CH:33][C:21]1=2)=[O:46])([CH3:51])([CH3:50])[CH3:49]

参加物

6

反応物 4

HCID 962WaterHCID 516920Potassium bisulfateHCID 56777373H-Gly-otbu acohHCID 85633486HCID 85633486、化合物

生成物 1

HCID 15020966HCID 15020966、化合物収率 79%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a solution of 17-tetrabenzo(a,c,g,i)fluorenylmethyl-p-nitrophenyl carbonate (39.2 mg, 0.07 mmol) and glycine tert-butyl ester acetate salt (14.7 mg, 0.077 mmol; 1.1 equiv.) in dichloromethane (1.5 ml) was added N,N′-dimethyl aniline (18 μl, 0.14 mmol; 2 equiv). The reaction mixture was stirred at room temperature, under nitrogen, for 72 h. After addition of water (10 ml) and acidification with KHSO4 (2M; pH=1), the reaction mixture was extracted with dichloromethane (3×15 ml), washed with water (3×20 ml) and dried over MgSO4. The solvent was removed in vacuo to give an orange oil which was triturated in ether. A yellow solid was obtained which was filtered, washed with petrol (b.p. 40-60° C.) and dried to give compound (42) (30.6 mg, 79%); m.p. 170-171° C.; (Found: C, 79.7; H, 5.51; N, 2.33; C37H31NO4 requires: C, 80.3; H, 5.60; N, 2.53%); t.l.c. Rf (H) 0.79, Rf (I) 0.95; νmax (CH2Cl2) 3440 (secondary amide NH), 3060 (CH stretching, aromatic), 2940 (CH stretching, alkyl), 175 (CO, urethane, ester and slide I), 1600, 1500 (aromatic rings), 1520 (amide II), 1340 (OH bonding) cm−1, 1220, 1160, 1110 (CO stretching), 865, 850 (out of plane CH bonding); λmax 384 (16323), 367 (17656), 302 (42641), 290 (34313), 262 (62296) nm; δH (CDCl3, 80 MHz) 8.85-8.60 (6H, m, aromatic), 8.39-8.28 (2H, m, aromatic), 7.81-7.56 (8H, m, aromatic), 5.27 (1H, t, 3J=6 Hz, CH), 4.98 (1H, s broad, NH), 4.61 (2H, d, 3J=6 Hz, CH2), 3.74 (2H, d, 3J=6 Hz, CH2 glycine), 1.44 (9H, s, CH3×3); δc (CDCl3, 50 MHz) 168.7 (CO, ester), 156.1 (CO, urethane), 141.9, 136.7, 131.5, 130.3, 128.7, 127.9 (quaternary aromatic C's), 127.4, 126.8, 126.0, 125.8, 125.3, 124.9, 123.5, 123.1 (aromatic CH's), 82.0 (quaternary C, CMe3), 69.0 (CH2), 47.5 (CH), 43.2 (CH2, glycine), 27.9 (CH3×3); m/z (FAB) 553, 379. HRMS 553.22527, C37H31NO4 requires 553.22529 ( ) <1 ppm.

後処理

  1. extractionthe reaction mixture was extracted with dichloromethane (3×15 ml)
  2. washwashed with water (3×20 ml)
  3. dry with materialdried over MgSO4
  4. customThe solvent was removed in vacuo
  5. customto give an orange oil which
  6. customwas triturated in ether
  7. customA yellow solid was obtained which
  8. filtrationwas filtered
  9. washwashed with petrol (b.p. 40-60° C.)
  10. customdried

出典と根拠

ORDレコード
ord-a2425e45be9c4ba3ae98d6a656f76f4b
出典データセット
uspto-grants-2002_03
特許番号
US06359113B1

反応ノート

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