Trifluoroacetic acid → HCID 86604596, compound

HRID 603453Notes

Reaction equation

HRID 603453 reaction equation
[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].C(OC([NH:15][CH2:16][CH2:17][CH2:18][O:19][C:20]1[CH:21]=[C:22]2[C:26](=[CH:27][CH:28]=1)[C@H:25]([CH2:29][C:30]([O:32][CH2:33][CH3:34])=[O:31])[CH2:24][CH2:23]2)=O)(C)(C)C>C(Cl)Cl>[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[NH2:15][CH2:16][CH2:17][CH2:18][O:19][C:20]1[CH:21]=[C:22]2[C:26](=[CH:27][CH:28]=1)[C@H:25]([CH2:29][C:30]([O:32][CH2:33][CH3:34])=[O:31])[CH2:24][CH2:23]2

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59300472HCID 59300472, compound

Product 1

HCID 86604596HCID 86604596, compoundYield 107%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (4.03 mL, 51.9 mmol) was added to a solution of ethyl ((1S)-5-{3-[(tert-butoxycarbonyl)amino]propoxy}-2,3-dihydro-1H-inden-1-yl)acetate (Example 262, 2.47 g, 6.54 mmol) in CH2Cl2 (32 mL). The mixture was stirred at rt for 18 h, and then concentrated under reduced pressure to give the product as a viscous oil (2.74 g, 94%). 1H NMR (400 MHz, CD2Cl2) δ 7.86 (b, 3H), 7.05 (d, 1H), 6.76 (d, 1H), 6.68 (dd, 1H), 4.15 (q, 2H), 4.08 (t, 2H), 3.49 (qt, 1H), 3.32-3.20 (m, 2H), 2.92-2.78 (m, 2H), 2.67 (dd, 1H), 2.45-2.32 (m, 2H), 2.16 (qt, 2H), 1.80-1.70 (m, 1H), 1.28 (t, 3H).

Workup

  1. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-0e7f871936d64ca2896d21f9d2301ac0
Source dataset
uspto-grants-2011_03
Patent number
US07906653B2

Reaction notes

Loading…