ホームMCPワークベンチSkills
ホームワークベンチ通知マイページ
llms.txt · MCPガイドプライバシーポリシー · 利用規約 · サポートv1.8.0
  1. ホーム
  2. /反応

Dimethylformamide → (R)-N2-[N-[(1,1-Dimethylethoxy)carbonyl]-4-nitro-L-phenylalanyl]-N-(1-methyl-2-phenylethyl)-L-allothreoninamide

HRID 864098
ノート
印刷プレビュー

反応式

HRID 864098 の反応式
[C:1]([NH:8][C@H:9](C(O)=O)[CH2:10][C:11]1[CH:16]=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[CH:13][CH:12]=1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[OH2:23].ON1[C:29]2C=CC=C[C:28]=2N=N1.Cl.CN(C)[CH2:37][CH2:38][CH2:39][CH2:40][CH2:41]N=C=N.[C:46](O)([C:48](F)(F)F)=[O:47].C[N:54]1[CH2:59]CO[CH2:56][CH2:55]1.[Cl-].[Na+].O.O.C[N:65]([CH3:68])[CH:66]=[O:67]>>[CH3:7][C:4]([CH3:5])([O:3][C:1]([NH:8][C@H:9]([C:66]([NH:65][C@@H:68]([C:59]([NH:54][CH:55]([CH3:56])[CH2:37][C:38]1[CH:29]=[CH:28][CH:41]=[CH:40][CH:39]=1)=[O:23])[C@H:46]([CH3:48])[OH:47])=[O:67])[CH2:10][C:11]1[CH:12]=[CH:13][C:14]([N+:17]([O-:19])=[O:18])=[CH:15][CH:16]=1)=[O:2])[CH3:6]
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 7

HCID 6228Dimethylformamide2 回HCID 6422Trifluoroacetic acidHCID 79724-MethylmorpholineHCID 27960291-Hydroxybenzotriazole hydrateHCID 7021882N-(tert-Butoxycarbonyl)-4-nitro-L-phenylalanineHCID 23713072Sodium chloride dihydrate
HCID 57482816
1-(3-Dimethylaminopropyl)-2-ethylcarbodiimide hydrochloride

生成物 1

HCID 131719590(R)-N2-[N-[(1,1-Dimethylethoxy)carbonyl]-4-nitro-L-phenylalanyl]-N-(1-methyl-2-phenylethyl)-L-allothreoninamide収率 98%

実験手順

To a solution of Part A compound (0.418 g, 1.29 mmol, 1.00 eq.) in dichloromethane (2.2 mL) under argon at 0° C. was added trifluoroacetic acid (1.5 mL, 19.5 mmol, 15.1 eq.). After 4.0 hr, trifluoroacetic acid (5 mL, 64.8 mmol, 5.44 eq.) was added. After 5 hr, the reaction mixture was concentrated in vacuo to give the crude TFA salt of Part A compound. To a solution of Boc-4-nitro-L-phenylalanine (0.441 g, 1.42 mmol, 1.10 eq.) and 1-hydroxybenzo-triazole hydrate (0.193 g, 1.43 mmol, 1.10 eq.) in dimethylformamide (5.0 mL) at 0° C. was added 1-(3-dimethylaminopropyl)-2-ethylcarbodiimide hydrochloride (0.273 g, 1.43 mmol, 1.10 eq.). After 0.5 hr, a solution of crude TFA salt of Part A compound (1.29 mmol, 1.00 eq.) in dimethylformamide (3.0 mL) was added, which was then followed by 4-methylmorpholine (0.5 mL, 4.55 mmol, 3.52 eq.). After 21 hr, the reaction mixture was poured into a brine/water solution (1:1) and extracted with ethyl acetate twice. The organic layers were combined and washed with aqueous 0.25M potassium hydrogen sulfate, water, aqueous saturated sodium bicarbonate and water, successively. The organic layer was concentrated in vacuo to give title compound (0.651 g, 98.0%):

後処理

  1. waitAfter 21 hr
  2. extractionextracted with ethyl acetate twice
  3. washwashed with aqueous 0.25M potassium hydrogen sulfate, water, aqueous saturated sodium bicarbonate and water
  4. concentrationThe organic layer was concentrated in vacuo

出典と根拠

ORDレコード
ord-6517ef4b1f8d4574806198650a083288
出典データセット
uspto-grants-1996_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05561146

反応ノート

読み込み中…

このページの内容参加物実験手順後処理出典と根拠反応ノート