Trifluoroacetic acid → HCID 86757032, compound

HRID 1068218Notes

Reaction equation

[C:1]([C:5]1[CH:10]=[CH:9][N:8]2[C:11]([CH:14]3[CH2:19][CH2:18][N:17]([CH2:20][C@@H:21]4[C@@H:25]([C:26]5[CH:31]=[CH:30][CH:29]=[C:28]([F:32])[CH:27]=5)[CH2:24][N:23]([C@@:33]([CH:47]5[CH2:50][CH2:49][CH2:48]5)([CH3:46])[C:34]([O:36]CC5C=CC(OC)=CC=5)=[O:35])[CH2:22]4)[CH2:16][CH2:15]3)=[CH:12][N:13]=[C:7]2[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].C(O)(C(F)(F)F)=O.C1(OC)C=CC=CC=1>>[C:1]([C:5]1[CH:10]=[CH:9][N:8]2[C:11]([CH:14]3[CH2:15][CH2:16][N:17]([CH2:20][C@@H:21]4[C@@H:25]([C:26]5[CH:31]=[CH:30][CH:29]=[C:28]([F:32])[CH:27]=5)[CH2:24][N:23]([C@@:33]([CH:47]5[CH2:48][CH2:49][CH2:50]5)([CH3:46])[C:34]([OH:36])=[O:35])[CH2:22]4)[CH2:18][CH2:19]3)=[CH:12][N:13]=[C:7]2[CH:6]=1)([CH3:2])([CH3:3])[CH3:4]

Participants

Reactant 3

HCID 6422Trifluoroacetic acid

HCID 7519Anisole

HCID 86757033HCID 86757033, compound

Product 1

HCID 86757032HCID 86757032, compoundYield 91.1%

Procedure

The title compound was prepared from 40 mg of α-(R)-(3-(S)-((4-(7-t-butyl-imidazo[1,2-a]pyridin-3-yl)-piperidine-1-yl)methyl)-4-(S)-(3-fluorophenyl) pyrrolidin-1-yl)-cyclobutylpropanoic acid, 4-methoxy-benzyl ester (from Step D), 2 mL of TFA and 0.4 mL of anisole, using a procedure analogous to that described in Example 235, Step D to provide 30 mg of the title compound as a foamy solid. ESI-MS 561 (M+H); HPLC A 1.92 min.

Sources & evidence

ORD record: ord-164a80a72fff4f35b2dce622cb14846a
Source dataset: uspto-grants-2001_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06248755B1

Reaction notes

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