Trifluoroacetic acid → HCID 68543977, compound

HRID 1943301Notes

Reaction equation

HRID 1943301 reaction equation
[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[CH2:8]([O:15][C:16]([NH:18][CH2:19][CH2:20][CH2:21][CH2:22][C@@H:23]([NH:34][C:35](=[O:57])[NH:36][C@@H:37]([CH2:45][CH2:46][CH2:47][CH2:48][NH:49]C(OC(C)(C)C)=O)[C:38]([O:40]C(C)(C)C)=[O:39])[C:24](=[O:33])[NH:25][C@H:26]([C:30](=[O:32])[NH2:31])[CH:27]([CH3:29])[CH3:28])=[O:17])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[NH2:49][CH2:48][CH2:47][CH2:46][CH2:45][C@H:37]([NH:36][C:35]([NH:34][C@@H:23]([C:24](=[O:33])[NH:25][C@H:26]([C:30](=[O:32])[NH2:31])[CH:27]([CH3:28])[CH3:29])[CH2:22][CH2:21][CH2:20][CH2:19][NH:18][C:16]([O:15][CH2:8][C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1)=[O:17])=[O:57])[C:38]([OH:40])=[O:39]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68546704HCID 68546704, compound

Product 1

HCID 68543977HCID 68543977, compoundYield 70.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-Butyl(S)-2-{3-[(R)-5-benzyloxycarbonylamino-1-((S)-1-carbamoyl-2-methyl-propylcarbamoyl)-pentyl]-ureido}-6-tert-butoxycarbonylaminohexanoate trifluoroacetate (37 mg, 0.045 mmol) was dissolved in 5 ml of CH2Cl2 and 1 ml of TFA and stirred at RT for 14 h. Preparative HPLC afforded 21 mg (70%) of (S)-6-amino-2-{3-[(R)-5-benzyloxycarbonylamino-1-((S)-1-carbamoyl-2-methyl-propylcarbamoyl)-pentyl]-ureido}-hexanoic acid trifluoroacetate.

Sources & evidence

ORD record
ord-5bbbdf99aa444f81b86ee9fe7d3ee451
Source dataset
uspto-grants-2013_03
Patent number
US08389764B2

Reaction notes

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