Triethylamine → HCID 20765639、化合物

HRID 984497ノート

反応式

HRID 984497 の反応式
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[S:9][C:10]1[CH:15]=[CH:14][C:13](/[CH:16]=[CH:17]/[C:18]([N:20]2[CH2:31][CH2:30][C:23]3([NH:27]C(=O)N[C:24]3=[O:29])[CH2:22][CH2:21]2)=[O:19])=[C:12]([Cl:32])[C:11]=1[Cl:33].[O:34](C(OC(C)(C)C)=O)C(OC(C)(C)C)=O.C(N(CC)CC)C.[OH-].[Na+]>COCCOC.CN(C1C=CN=CC=1)C.O>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[S:9][C:10]1[CH:15]=[CH:14][C:13](/[CH:16]=[CH:17]/[C:18]([N:20]2[CH2:31][CH2:30][C:23]([NH2:27])([C:24]([OH:34])=[O:29])[CH2:22][CH2:21]2)=[O:19])=[C:12]([Cl:32])[C:11]=1[Cl:33]

参加物

8

反応物 4

HCID 8471Triethylamine2 回HCID 14798Sodium HydroxideHCID 90495Di-tert-butyl dicarbonateHCID 20765643HCID 20765643、化合物

生成物 1

HCID 20765639HCID 20765639、化合物収率 45%

試薬・触媒・溶媒 3

HCID 142844-(Dimethylamino)pyridine触媒2 回HCID 962Water溶媒HCID 80711,2-Dimethoxyethane溶媒3 回

実験手順

To a suspension of Example 355 (700 mg, 1.4 mmol) in DME (10 mL) was added a solution of (BOC)2O (1.51 g, 6.9 mmol) in DME (5 mL), triethylamine (0.23 mL, 1.7 mmol) and DMAP (9 mg, 0.07 mmol). The reaction mixture was stirred at room temperature overnight. Additional triethylamine (0.23 mL) and DMAP (30 mg) were added, and the mixture was heated at 60° C. for 6 hours. After aqueous work up, the crude product was suspended in DME (5 mL) and water (5 mL) containing 200 mg of NaOH. The suspension was stirred for 5 hours at room temperature, and separated by HPLC to give the title compound (300 mg, 45%). 1H NMR (300 MHz, DMSO-d6) δ 1.78 (m, 2H), 2.10 (m, 2H), 3.60 (m, 2H), 3.80 (s, 3H), 3.86 (m, 2H), 6.58 (d, 1H), 7.10 (d, 1H), 7.25 (d, 1H), 7.28 (d, 1H), 7.50 (d, 1H), 7.58 (t, 1H), 7.77 (d, 1H), 7.80 (d, 1H), 8.50 (br s, 2H). MS (ESI+) m/z 481 (M+H)+. Anal calcd for C22H22N2Cl2SO4.0.75H2O: C, 47.34; H, 4.06; N, 4.60. Found: C, 47.31; H, 4.05; N, 4.43.

後処理

  1. temperaturethe mixture was heated at 60° C. for 6 hours
  2. stirringThe suspension was stirred for 5 hours at room temperature
  3. customseparated by HPLC

出典と根拠

ORDレコード
ord-403dc7d0ffbc4740ad9a45d5f337e35d
出典データセット
uspto-grants-2005_03
特許番号
US06867203B2

反応ノート

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