Trifluoroacetic acid → HDTrp-Leu-MetNH2 trifluoroacetate

HRID 2418613

反応式

HRID 2418613 の反応式
[NH:1](C(OC(C)(C)C)=O)[C@@H:2]([C:13]([NH:15][C@H:16]([C:21]([NH:23][C@H:24]([C:29]([NH2:31])=[O:30])[CH2:25][CH2:26][S:27][CH3:28])=[O:22])[CH2:17][CH:18]([CH3:20])[CH3:19])=[O:14])[CH2:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[NH:6][CH:5]=1.[F:39][C:40]([F:45])([F:44])[C:41]([OH:43])=[O:42]>C(SC)C.C(S)(S)C>[NH2:1][C@@H:2]([C:13]([NH:15][C@H:16]([C:21]([NH:23][C@H:24]([C:29]([NH2:31])=[O:30])[CH2:25][CH2:26][S:27][CH3:28])=[O:22])[CH2:17][CH:18]([CH3:20])[CH3:19])=[O:14])[CH2:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[NH:6][CH:5]=1.[F:39][C:40]([C:41]([OH:43])=[O:42])([F:45])[F:44]

参加物

5

反応物 2

HCID 6422Trifluoroacetic acidHCID 131713756BocDTrp-Leu-MetNH2

生成物 1

HCID 131713755HDTrp-Leu-MetNH2 trifluoroacetate収率 23%

試薬・触媒・溶媒 2

HCID 12230Ethyl methyl sulfide溶媒HCID 336451,1-Ethanedithiol溶媒

実験手順

Condensation of BocDTrpOPFP (8.60 g.) and HLeu-MetNH2 hydrochloride salt (Example 1, 5.44 g.) by the activated ester method gave BocDTrp-Leu-MetNH2 in 67% yield. De-t-butoxycarbonylation of BocDTrp-Leu-MetNH2 (6.69 g.) using trifluoroacetic acid in methyl ethyl sulfide and ethanedithiol gave HDTrp-Leu-MetNH2 trifluoroacetate salt in 23% yield.

出典と根拠

ORDレコード
ord-61fdc32b2888445d9cfb55f8896090df
出典データセット
uspto-grants-1984_09
特許番号
US04472305

関連ノート

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