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

HRID 863791Notes

Reaction equation

HRID 863791 reaction equation
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]

Participants

8

Reactant 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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

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.

Workup

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

Sources & evidence

ORD record
ord-fb064168584d4b17be4e4e9d636d4bb2
Source dataset
uspto-grants-1996_10
Patent number
US05561112

Reaction notes

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