Trifluoroacetic acid → (R)-1-(4-amino-3-chloro-5-trifluoromethyl-benzyl)-2-[4-(ethoxycarbonylmethyl-amino)-1,4'-bipiperidinyl-1'-yl]-2-oxo-ethyl 4-(2-oxo-1,2,4,5-tetrahydro-1,3-benzodiazepin-3-yl)-piperidine-1-carboxylate

HRID 2106521Notes

Reaction equation

HRID 2106521 reaction equation
C(O)(C(F)(F)F)=O.[O:8]=[C:9]1[N:15]([CH:16]2[CH2:21][CH2:20][N:19]([C:22]([O:24][C@H:25]([CH2:54][C:55]3[CH:60]=[C:59]([C:61]([F:64])([F:63])[F:62])[C:58]([NH2:65])=[C:57]([Cl:66])[CH:56]=3)[C:26]([N:28]3[CH2:33][CH2:32][CH:31]([N:34]4[CH2:39][CH2:38][CH:37]([N:40](C(OCC)=O)[CH2:41][C:42]([O:44][C:45](C)(C)[CH3:46])=[O:43])[CH2:36][CH2:35]4)[CH2:30][CH2:29]3)=[O:27])=[O:23])[CH2:18][CH2:17]2)[CH2:14][CH2:13][C:12]2[CH:67]=[CH:68][CH:69]=[CH:70][C:11]=2[NH:10]1>C(Cl)Cl>[O:8]=[C:9]1[N:15]([CH:16]2[CH2:17][CH2:18][N:19]([C:22]([O:24][C@H:25]([CH2:54][C:55]3[CH:60]=[C:59]([C:61]([F:62])([F:63])[F:64])[C:58]([NH2:65])=[C:57]([Cl:66])[CH:56]=3)[C:26]([N:28]3[CH2:29][CH2:30][CH:31]([N:34]4[CH2:39][CH2:38][CH:37]([NH:40][CH2:41][C:42]([O:44][CH2:45][CH3:46])=[O:43])[CH2:36][CH2:35]4)[CH2:32][CH2:33]3)=[O:27])=[O:23])[CH2:20][CH2:21]2)[CH2:14][CH2:13][C:12]2[CH:67]=[CH:68][CH:69]=[CH:70][C:11]=2[NH:10]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86611123(R)-1-(4-amino-3-chloro-5-trifluoromethyl-benzyl)-2-[4-(tert-butoxycarbonyl-ethoxycarbonyl-methylamino)-1,4'-bipiperidinyl-1'-yl]-2-oxo-ethyl 4-(2-oxo-1,2,4,5-tetrahydro-1,3-benzodiazepin-3-yl)-piperidine-1-carboxylate

Product 1

HCID 16044977(R)-1-(4-amino-3-chloro-5-trifluoromethyl-benzyl)-2-[4-(ethoxycarbonylmethyl-amino)-1,4'-bipiperidinyl-1'-yl]-2-oxo-ethyl 4-(2-oxo-1,2,4,5-tetrahydro-1,3-benzodiazepin-3-yl)-piperidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

0.5 mL TFA were added to a solution of 330 mg (0.36 mmol) (R)-1-(4-amino-3-chloro-5-trifluoromethyl-benzyl)-2-[4-(tert-butoxycarbonyl-ethoxycarbonyl-methylamino)-1,4′-bipiperidinyl-1′-yl]-2-oxo-ethyl 4-(2-oxo-1,2,4,5-tetrahydro-1,3-benzodiazepin-3-yl)-piperidine-1-carboxylate in 5 mL DCM cooled to 0° C. and the reaction mixture was stirred overnight at RT. It was evaporated down i. vac. and the residue was purified by HPLC. The fractions containing the product were combined and freeze-dried.

Workup

  1. customIt was evaporated down i
  2. customand the residue was purified by HPLC
  3. additionThe fractions containing the product
  4. customfreeze-dried

Sources & evidence

ORD record
ord-0cc67cae22af4576af4d858c404ddcc2
Source dataset
uspto-grants-2009_08
Patent number
US07579341B2

Reaction notes

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