Hydrochloric Acid → N-(2,6-Dichlorobenzoyl)-4-nitro-L-phenylalanine

HRID 16922

反応式

HRID 16922 の反応式
[N+:1]([C:4]1[CH:15]=[CH:14][C:7]([CH2:8][C@@H:9]([C:11]([OH:13])=[O:12])[NH2:10])=[CH:6][CH:5]=1)([O-:3])=[O:2].[OH-].[Na+].[Cl:18][C:19]1[CH:27]=[CH:26][CH:25]=[C:24]([Cl:28])[C:20]=1[C:21](Cl)=[O:22].Cl>CC(C)=O.O>[Cl:18][C:19]1[CH:27]=[CH:26][CH:25]=[C:24]([Cl:28])[C:20]=1[C:21]([NH:10][C@H:9]([C:11]([OH:13])=[O:12])[CH2:8][C:7]1[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:15][CH:14]=1)=[O:22]

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 137064-Nitro-3-phenyl-L-alanineHCID 14798Sodium Hydroxide2 回HCID 783922,6-Dichlorobenzoyl chloride

生成物 1

HCID 58018322N-(2,6-Dichlorobenzoyl)-4-nitro-L-phenylalanine収率 97.5%

試薬・触媒・溶媒 2

HCID 180Acetone溶媒HCID 962Water溶媒

反応条件

温度
10 °C

実験手順

200 mL of water and 91 mL of acetone were mixed and 72.4 g (344 mmol) of 4-nitro-L-phenylalanine was added thereto and cooled down to 10° C. or lower. 68 mL of 6M sodium hydroxide aqueous solution was added dropwise to the solution so that the temperature thereof did not exceed 15° C. Keeping around pH 14, 73.58 g (344 mmol) of 2,6-dichlorobenzoyl chloride was slowly added dropwise thereto. In order to keep around pH 14, if needed, a sodium hydroxide aqueous solution was added dropwise. 2 hours later of completion of drop, 86 mL of 6M hydrochloric acid was added with keeping the temperature of the reaction solution at 15° C. or lower to precipitate white crystals. After maturing at 10° C. or lower, the crystals were separated, dried under reduced pressure at 60° C. to obtain 128.5 g of Nα-(2,6-dichlorobenzoyl)-4-nitro-L-phenylalanine. (Yield: 97%) 1H NMR (400 MHz, DMSO-d6): 9.12 (d, 1H, J=8.42 Hz), 8.16 (d, 2H, J=8.78 Hz), 7.59 (d, J=8.77Hz), 7.42 (m, 3H), 3.29 (m), 3.07 (dd, 1H, J=3.64 and 10.42 Hz). 13C NMR (100 MHz, DMSO-d6): 172.25, 163.74, 146.68, 146.18, 131.51, 131.37, 131.05, 128.37, 123.55, 53.17, 36.74.

後処理

  1. customthereof did not exceed 15° C
  2. additionwas slowly added dropwise
  3. customat 15° C.
  4. customlower to precipitate white crystals
  5. customAfter maturing at 10° C.
  6. customlower, the crystals were separated
  7. customdried under reduced pressure at 60° C.

出典と根拠

ORDレコード
ord-fe3a8c7c105a458f97a5dc0c5bd7a085
出典データセット
uspto-grants-2010_06
特許番号
US07737274B2

関連ノート

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