Hydrochloric Acid → Ac-D-Lys(Z)-D-Pro-D-Val-NH2

HRID 2245217

反応式

HRID 2245217 の反応式
[NH:1]([C:28]([CH3:30])=[O:29])[C@@H:2]([C:18]([N:20]1[CH2:27][CH2:26][CH2:25][C@@H:21]1[C:22]([OH:24])=O)=[O:19])[CH2:3][CH2:4][CH2:5][CH2:6][NH:7][C:8]([O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:9].Cl.[NH2:32][C@@H:33]([C:37]([NH2:39])=[O:38])[CH:34]([CH3:36])[CH3:35].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(C(C)C)C(C)C)C>CN(C=O)C>[NH:1]([C:28]([CH3:30])=[O:29])[C@@H:2]([C:18]([N:20]1[CH2:27][CH2:26][CH2:25][C@@H:21]1[C:22]([NH:32][C@@H:33]([C:37]([NH2:39])=[O:38])[CH:34]([CH3:36])[CH3:35])=[O:24])=[O:19])[CH2:3][CH2:4][CH2:5][CH2:6][NH:7][C:8]([O:10][CH2:11][C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)=[O:9]

参加物

7

反応物 5

HCID 313Hydrochloric AcidHCID 81531DiisopropylethylamineHCID 444079(R)-2-amino-3-methylbutanamideHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 131727990Ac-D-Lys(Z)-D-Pro-OH

生成物 1

HCID 131727991Ac-D-Lys(Z)-D-Pro-D-Val-NH2

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
5 °C

実験手順

In an inert thermostable reactor provided with a mechanical stirrer, 94.25 g of Ac-D-Lys(Z)-D-Pro-OH (XI) (224.7 mmol) are introduced followed by 470 ml of DMF. 32.58 g of HCl. H-D-Val-NH2 (V) (213.5 mmol, 0.95 eq) and 85.22 g of HBTU (1 eq) are then added. The medium is cooled down to 5° C., and 96.6 ml of ethyldiisopropylamine (2.5 eq) are added dropwise within 15 minutes. This is allowed to reach 0° C. again and after 1.30 to 2 hours, a strong crystallization could be observed. The reaction completion is CCM controlled. The reaction medium is then poured onto 2350 ml of AcOEt, stirred for 15 minutes, filtered and washed successively with 470 ml of AcOEt and 470 ml of diisopropyl ether. The derivate (XII) is vacuum dried at 25° C. This way, 107.2 g (92%) pf Ac-D-Lys(Z)-D-Pro-D-Val-NH2 are obtained.

後処理

  1. customIn an inert thermostable reactor provided with a mechanical stirrer
  2. customto reach 0° C.
  3. customa strong crystallization
  4. additionThe reaction medium is then poured onto 2350 ml of AcOEt
  5. filtrationfiltered
  6. washwashed successively with 470 ml of AcOEt and 470 ml of diisopropyl ether
  7. customdried at 25° C

出典と根拠

ORDレコード
ord-4ba63546249646fb9ba69a24b15dfec2
出典データセット
uspto-grants-2010_03
特許番号
US07683026B2

関連ノート

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