Trifluoroacetic acid → R-Lotrafiban

HRID 1953760Notes

Reaction equation

HRID 1953760 reaction equation
[N:1]1([C:13]([C:15]2[CH:16]=[CH:17][C:18]3[NH:24][C@H:23]([CH2:25][C:26]([O-:28])=[O:27])[C:22](=[O:29])[N:21]([CH3:30])[CH2:20][C:19]=3[CH:31]=2)=[O:14])[CH2:6][CH2:5][CH:4]([CH:7]2[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]2)[CH2:3][CH2:2]1.C(C(O)=O)(F)(F)F.N1(C(C2C=CC3N[C@@H](CC([O-])=O)C(=O)N(C)CC=3C=2)=O)CCC(C2CCNCC2)CC1>O.C(#N)C>[N:1]1([C:13]([C:15]2[CH:16]=[CH:17][C:18]3[NH:24][C@H:23]([CH2:25][C:26]([OH:28])=[O:27])[C:22](=[O:29])[N:21]([CH3:30])[CH2:20][C:19]=3[CH:31]=2)=[O:14])[CH2:6][CH2:5][CH:4]([CH:7]2[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]2)[CH2:3][CH2:2]1

Participants

6

Reactant 3

HCID 6422Trifluoroacetic acid2×HCID 86755832HCID 86755832, compoundHCID 86755833HCID 86755833, compound

Product 1

HCID 10693833R-Lotrafiban

Reagents, catalysts & solvents 2

HCID 962WaterSolvent4×HCID 6342AcetonitrileSolvent4×

Procedure

Using the procedure of Preparation 8(j), except substituting the compounds of Example 26(b) and 27(b) for the compound of Preparation 8(i) gave the following compounds: 26(c). (R)-7-[(4,4'-bipiperidin-1-yl)carbonyl]-2,3,4,5-tetrahydro-4-methyl-3-oxo-1H-1,4-benzodiazepine-2-acetate: [α]D +92.4 (c 0.5,CH3OH); MS(ES) m/e 429 [M+H]+ ; 427 [M-H]- ; HPLC tR 12.7 min (Ultrasphere C18, 4.6×250 mm, 1.5 mL/min, gradient, A:acetonitrile B: water-0.1% TFA, 5-60% acetonitrile over 20 min, UV detection at 220 nm); Anal. (C23H32N4O4.4.5 CF3CO2H.3.33 H2O) calcd: C, 37.44; H, 4.16; N, 5.29. found: C, 37.43; H, 3.81; N, 5.20. 27(c). (S)-7-[(4,4'-bipiperidin-1-yl)carbonyl]-2,3,4,5-tetrahydro-4-methyl-3-oxo-1H-1,4-benzodiazepine-2-acetate: [α]D -105.9 (c 0.6,CH3OH); MS(ES) m/e 429 [M+H]+ ; 427 [M-H]- ; HPLC tR 12.6 min (Ultrasphere C18, 4.6×250 mm, 1.5 mL/min, gradient, A:acetonitrile B: water-0.1% TFA, 5-60% acetonitrile over 20 min, UV detection at 220 nm); Anal. (C23H32N4O4.3 CF3CO2H.1.25 H2O) calcd: C, 43.92; H, 4.77; N, 7.06. found: C, 44.09; H, 5.00; N, 7.29.

Workup

  1. customgave the following compounds

Sources & evidence

ORD record
ord-49b4559be1fb4d6fa3b9ecfb0af2878f
Source dataset
uspto-grants-2000_09
Patent number
US06117866

Reaction notes

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