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

HRID 1732523
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HRID 1732523 반응식
[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
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 5

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-83288b81c18f488c859c673fe04e5fbf
출처 데이터셋
uspto-grants-1980_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04237046

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