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1-Hydroxybenzotriazole → t-Butyloxycarbonyl-L-methionyl-L-alanyl-L-valyl-Nepsilon-benzyloxycarbonyl-L-lysine benzyl ester

HRID 1732523
ノート
印刷プレビュー

反応式

HRID 1732523 の反応式
[CH2:1]([O:8][C:9](=[O:46])[C@H:10]([CH2:31][CH2:32][CH2:33][CH2:34][NH:35][C:36]([O:38][CH2:39][C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)=[O:37])[NH:11][C:12](=[O:30])[C@H:13]([CH:27]([CH3:29])[CH3:28])[NH:14][C:15](=[O:26])[C@H:16]([CH3:25])NC(OC(C)(C)C)=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.FC(F)(F)C([O-])=O.[NH:54]([C:72]([O:74][C:75]([CH3:78])([CH3:77])[CH3:76])=[O:73])[C@H:55]([C:60](OC1C=CC([N+]([O-])=O)=CC=1)=[O:61])[CH2:56][CH2:57][S:58][CH3:59].CC[N:81](C(C)C)C(C)C.C1C=CC2N(O)N=NC=2C=1>CN(C=O)C>[CH2:1]([O:8][C:9](=[O:46])[C@H:10]([CH2:31][CH2:32][CH2:33][CH2:34][NH:35][C:36]([O:38][CH2:39][C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)=[O:37])[NH:11][C:12](=[O:30])[C@H:13]([CH:27]([CH3:28])[CH3:29])[NH:14][C:15](=[O:26])[C@H:16]([CH3:25])[NH:81][C:60](=[O:61])[C@H:55]([CH2:56][CH2:57][S:58][CH3:59])[NH:54][C:72]([O:74][C:75]([CH3:78])([CH3:77])[CH3:76])=[O:73])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1
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 5

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 84468TrifluoroacetateHCID 7021880Boc-Met-ONpHCID 131711964t-Butyloxycarbonyl-L-alanyl-L-valyl-Nepsilon-benzyloxycarbonyl-L-lysine benzyl ester

生成物 1

HCID 86737377
t-Butyloxycarbonyl-L-methionyl-L-alanyl-L-valyl-Nepsilon-benzyloxycarbonyl-L-lysine benzyl ester

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

Partial deprotection of compound XXI (3.4 g, 5.3 mmole) was carried out as described in the previous paragraph. The trifluoroacetate salt (RfC, 0.75) was acylated in DMF (50 ml) with Boc-L-Met-ONp (2.18 g, 5.9 mmole, Bachem) in the presence of DIEA (1.9 ml, 12 mmole) and HOBt (0.9 g, 5.9 mmole). After 4 hr at room temperature the reaction was complete. Evaporation of most of the solvent in vacuo was followed by trituration with EtOAc. The precipitate was washed with EtOAc, with ether and dried: 3.8 g (93%); m.p. 169°-171° C., [α]D24 -21.5° (c 1.2, DMF) RfK, 0.65; RfI, 0.52.

後処理

  1. customEvaporation of most of the solvent in vacuo
  2. washThe precipitate was washed with EtOAc, with ether
  3. customdried

出典と根拠

ORDレコード
ord-83288b81c18f488c859c673fe04e5fbf
出典データセット
uspto-grants-1980_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US04237046

反応ノート

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