Dicyclohexylcarbodiimide → HCID 70050906, compound

HRID 863792Notes

Reaction equation

HRID 863792 reaction equation
C([NH:8][C:9]([C:11]1[CH:19]=[CH:18][C:14]([C:15]([OH:17])=O)=[CH:13][CH:12]=1)=[NH:10])(OC(C)(C)C)=O.C(N[C:28]([C:30]1[CH:35]=[CH:34][C:33]([CH2:36][C:37]([OH:39])=[O:38])=CC=1)=[NH:29])(OC(C)(C)C)=O.[CH:40]1[CH:41]=CC2N(O)N=NC=2[CH:45]=1.C1CCC([N:56]=C=NC2CCCCC2)CC1.[C:65]([OH:71])([C:67]([F:70])([F:69])[F:68])=[O:66].C1(OC)C=CC=CC=1>C(N(CC)CC)C>[F:68][C:67]([F:70])([F:69])[C:65]([OH:71])=[O:66].[CH3:45][CH:40]([CH3:41])[CH2:67][C:65]([NH:56][C@@H:33]([CH2:34][CH2:35][CH2:30][CH2:28][NH:29][C:15](=[O:17])[C:14]1[CH:13]=[CH:12][C:11]([C:9](=[NH:10])[NH2:8])=[CH:19][CH:18]=1)[CH2:36][C:37]([OH:39])=[O:38])=[O:66]

Participants

7

Reactant 5

HCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 66633105Anisole trifluoroacetic acidHCID 135741236HCID 135741236, compoundHCID 135741367153074-92-1

Product 1

HCID 70050906HCID 70050906, compound

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

After hydrogenation of 2.2 g of the product from stage C) of example 6 analogously to stage C) of example 4, the product is further reacted with 1.34 g of N-Boc-p-amidinobenzoic acid (preparation analogously to N-Boc-p-amidinophenylacetic acid), 0.7 ml of triethylamine, 0.852 g of HOBT and 1.04 g of DCC, as in stage C) of example 4, and subsequently deprotected with 25 ml of TFA/anisole (95/5), and worked up, to produce the (S)-3-[N-(3-methylbutyryl)amino]-7-[N-(p-amidinobenzoyl)amino]heptanoic acid trifluoroacetate product in the form of a white powder; MS: 391 (M+H)+. The free compound is produced from the trifluoroacetate in known manner.

Sources & evidence

ORD record
ord-dba6e9f00aa34578a231bb13535bfd92
Source dataset
uspto-grants-1996_10
Patent number
US05561112

Reaction notes

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