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1,2-Dichloroethane → 3-methyl-D-valyl-N-[5-chloro-2-(1H-tetraazol-1-yl)benzyl]-L-prolinamide

HRID 857746
ノート
印刷プレビュー

反応式

HRID 857746 の反応式
C(OC([NH:8][C@@H:9]([C:14]([OH:16])=O)[C:10]([CH3:13])([CH3:12])[CH3:11])=O)(C)(C)C.[Cl:17][C:18]1[CH:19]=[CH:20][C:21]([N:33]2[CH:37]=[N:36][N:35]=[N:34]2)=[C:22]([CH:32]=1)[CH2:23][NH:24][C:25](=[O:31])[C@@H:26]1[CH2:30][CH2:29][CH2:28][NH:27]1.C(Cl)CCl.C1C=NC2N(O)N=NC=2C=1>CN(C=O)C.C(O)(C(F)(F)F)=O.C(Cl)Cl>[CH3:13][C:10]([CH3:11])([CH3:12])[C@H:9]([C:14]([N:27]1[CH2:28][CH2:29][CH2:30][C@H:26]1[C:25]([NH:24][CH2:23][C:22]1[CH:32]=[C:18]([Cl:17])[CH:19]=[CH:20][C:21]=1[N:33]1[CH:37]=[N:36][N:35]=[N:34]1)=[O:31])=[O:16])[NH2:8]
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 111,2-DichloroethaneHCID 181649HOAtHCID 7005057(2R)-2-{[(tert-butoxy)carbonyl]amino}-3,3-dimethylbutanoic acidHCID 69655818N-[5-chloro-2-(1H-tetraazol-1-yl)benzyl]-L-prolinamide

生成物 1

HCID 587601623-methyl-D-valyl-N-[5-chloro-2-(1H-tetraazol-1-yl)benzyl]-L-prolinamide

試薬・触媒・溶媒 2

HCID 6228
Dimethylformamide
溶媒
HCID 21863450Trifluoroacetic acid methylene chloride溶媒

実験手順

The title compound was prepared from N-(tert-butoxycarbonyl)-3-methyl-D-valine (53 mg, 0.23 mmol), N-[5-chloro-2-(1H-tetraazol-1-yl)benzyl]-L-prolinamide (Example 26, Step B, 87 mg, 0.23 mmol, 1.0 equiv), EDC (66 mg, 0.34 mmol, 1.5 equiv) and HOAt (16 mg, 0.11 mmol, 0.5 equiv) in DMF (1 mL) followed by deprotection in TFA-CH2Cl2 essentially according to the procedure described in Example 26, Step C. Purification by reverse phase chromatography [95:5 water (+0.1% TFA)/CH3CN (+0.1% TFA) to 50:50 water (+0.1% TFA)/CH3CN (+0.1% TFA)] followed by lyophilization of the fractions afforded the title compound as a white powder. 1H NMR (300 MHz, CDCl3): δ 9.22 (s, 1 H), 8.32–8.29 (m, 3 H), 7.85 (d, J=1.8 Hz, 1 H), 7.43 (dd, J=2.1, 8.4 Hz, 1 H), 7.15 (d, J=8.4 Hz, 1 H), 4.45 (app d, J=8.1 Hz, 1 H), 4.35–4.27 (m, 2 H), 3.95–3.79 (m, 2 H), 3.62–3.56 (m, 1 H), 2.31–2.25 (m, 1 H), 2.10–1.87 (m, 3 H), 1.18 (s, 9 H). HRMS (APCI) M+H: calculated for (C19H26N7O2Cl)+ 420.1910, found 420.1915.

後処理

  1. customPurification by reverse phase chromatography [95:5 water (+0.1% TFA)/CH3CN (+0.1% TFA) to 50:50 water (+0.1% TFA)/CH3CN (+0.1% TFA)]

出典と根拠

ORDレコード
ord-86c64e5a477f457ba7143c83d7895169
出典データセット
uspto-grants-2006_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07144899B2

反応ノート

読み込み中…

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