Triethylamine → 5-({(3-formylbenzyl)[(1S)-1,2,3,4-tetrahydro-1-naphthalenyl]amino}carbonyl)-1,2,4-benzenetricarboxylic Acid

HRID 2307692ノート

反応式

HRID 2307692 の反応式
[OH:1][CH2:2][C:3]1[CH:4]=[C:5]([CH:35]=[CH:36][CH:37]=1)[CH2:6][N:7]([C@@H:25]1[C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[CH2:28][CH2:27][CH2:26]1)[C:8]([C:10]1[CH:15]=[C:14]([C:16]([OH:18])=[O:17])[C:13]([C:19]([OH:21])=[O:20])=[CH:12][C:11]=1[C:22]([OH:24])=[O:23])=[O:9].C(N(CC)CC)C>CS(C)=O>[CH:2]([C:3]1[CH:4]=[C:5]([CH:35]=[CH:36][CH:37]=1)[CH2:6][N:7]([C@@H:25]1[C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[CH2:28][CH2:27][CH2:26]1)[C:8]([C:10]1[CH:15]=[C:14]([C:16]([OH:18])=[O:17])[C:13]([C:19]([OH:21])=[O:20])=[CH:12][C:11]=1[C:22]([OH:24])=[O:23])=[O:9])=[O:1]

参加物

4

反応物 2

HCID 8471TriethylamineHCID 101419005-({[3-(hydroxymethyl)benzyl][(1S)-1,2,3,4-tetrahydro-1-naphthalenyl]amino}carbonyl)-1,2,4-benzenetricarboxylic Acid

生成物 1

HCID 102288355-({(3-formylbenzyl)[(1S)-1,2,3,4-tetrahydro-1-naphthalenyl]amino}carbonyl)-1,2,4-benzenetricarboxylic Acid収率 75%

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

実験手順

The product from Example 76D (2.3 g, 4.6 mmol) and triethylamine (4.48 mL, 32.1 mmol) in DMSO (25 mL) was treated with sulfur trioxide pyridine complex (2.92 g, 18.4 mmol). After 5 hours, the mixture was partitioned between ethyl acetate and 1N HCl. The separated organic phase was washed with 1N HCl, brine, and concentrated under reduced pressure. The residue was dissolved in THF (30 mL) and saturated aqueous Na2CO3 solution (30 mL) was added. After stirring vigorously for 1 hour, the separated aqueous layer was acidified and extracted with ethyl acetate. The organic extracts were combined, washed with brine, dried (Na2SO4), filtered and the filtrate concentrated under reduced pressure to provide the title compound as a pale yellow solid (1.73 g).

後処理

  1. customthe mixture was partitioned between ethyl acetate and 1N HCl
  2. washThe separated organic phase was washed with 1N HCl, brine
  3. concentrationconcentrated under reduced pressure
  4. dissolutionThe residue was dissolved in THF (30 mL)
  5. additionsaturated aqueous Na2CO3 solution (30 mL) was added
  6. extractionextracted with ethyl acetate
  7. washwashed with brine
  8. dry with materialdried (Na2SO4)
  9. filtrationfiltered
  10. concentrationthe filtrate concentrated under reduced pressure

出典と根拠

ORDレコード
ord-4aaf0e0fbd3a4b21b8b1e6f05e8b5f2f
出典データセット
uspto-grants-2004_12
特許番号
US06831193B2

反応ノート

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