Trifluoroacetic acid → (S)-3-[N-(3-methylbutyryl)amino]-6-[N-(p-amidinophenylacetyl)amino]hexanoic acid trifluoroacetate

HRID 863791ノート

反応式

HRID 863791 の反応式
Cl.C[O:3][C:4](=[O:18])[CH2:5][C@@H:6]([NH:11][C:12](=[O:17])[CH2:13][CH:14]([CH3:16])[CH3:15])[CH2:7][CH2:8][CH2:9][NH2:10].C([NH:26][C:27]([C:29]1[CH:34]=[CH:33][C:32]([CH2:35][C:36](O)=[O:37])=[CH:31][CH:30]=1)=[NH:28])(OC(C)(C)C)=O.C1C=CC2N(O)N=NC=2C=1.C1CCC(N=C=NC2CCCCC2)CC1.[C:64]([OH:70])([C:66]([F:69])([F:68])[F:67])=[O:65].O[Li].O>C(N(CC)CC)C>[F:67][C:66]([F:69])([F:68])[C:64]([OH:70])=[O:65].[CH3:15][CH:14]([CH3:16])[CH2:13][C:12]([NH:11][C@@H:6]([CH2:7][CH2:8][CH2:9][NH:10][C:36](=[O:37])[CH2:35][C:32]1[CH:31]=[CH:30][C:29]([C:27](=[NH:26])[NH2:28])=[CH:34][CH:33]=1)[CH2:5][C:4]([OH:3])=[O:18])=[O:17]

参加物

8

反応物 6

HCID 6422Trifluoroacetic acidHCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 168937Lithium hydroxide, monohydrateHCID 86749878(S)-3-[N-(3-methylbutyryl)amino]-6-aminohexanoic acid methylester hydrochlorideHCID 135741367153074-92-1

生成物 1

HCID 70049485(S)-3-[N-(3-methylbutyryl)amino]-6-[N-(p-amidinophenylacetyl)amino]hexanoic acid trifluoroacetate

試薬・触媒・溶媒 1

HCID 8471Triethylamine溶媒

実験手順

560 mg of the product of stage A) of example 2 is dissolved in 20 ml of methanol and hydrogenated in the presence of 0.3 g of Pd/C (10%) and 1.41 ml of 1N hydrochloric acid. After working up as described in stage C) of example 1, (S)-3-[N-(3-methylbutyryl)amino]-6-aminohexanoic acid methylester hydrochloride is obtained in the form of a colourless oil. 400 mg of the hydrochloride and 392 mg of N-Boc-p-amidinophenylacetic acid, together with 0.2 ml of triethylamine, 259 mg of HOBT and 290 mg of DCC, are reacted and worked up as described in stage C) of example 1. After cleavage of the Boc group with TFA and hydrolysis of the methylester with LiOH-H2O analogously to stage C) of example 1, the crude product obtained is recrystallized from methanol. The (S)-3-[N-(3-methylbutyryl)amino]-6-[N-(p-amidinophenylacetyl)amino]hexanoic acid trifluoroacetate product is isolated as a white powder; MS: 391 (M+H)+. The free compound is obtained from the trifluoroacetate in known manner.

後処理

  1. customthe crude product obtained
  2. customis recrystallized from methanol

出典と根拠

ORDレコード
ord-fb064168584d4b17be4e4e9d636d4bb2
出典データセット
uspto-grants-1996_10
特許番号
US05561112

反応ノート

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