Trifluoroacetic acid → HCID 25065845, compound

HRID 1424621Notes

Reaction equation

HRID 1424621 reaction equation
COC1C=C(C=C(OC)C=1)C[NH:7][C:8]([C:10]12[CH2:19][CH:14]3[CH2:15][CH:16]([CH2:18][CH:12]([CH:13]3[O:20][C:21]([N:23]3[CH2:28][CH2:27][C:26]4([C:36]5[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=5)[CH:30]([CH2:37][C:38]([OH:40])=[O:39])[CH2:29]4)[CH2:25][CH2:24]3)=[O:22])[CH2:11]1)[CH2:17]2)=[O:9].C(O)(C(F)(F)F)=O>>[C:8]([C:10]12[CH2:19][CH:14]3[CH2:15][CH:16]([CH2:18][CH:12]([CH:13]3[O:20][C:21]([N:23]3[CH2:28][CH2:27][C:26]4([C:36]5[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=5)[CH:30]([CH2:37][C:38]([OH:40])=[O:39])[CH2:29]4)[CH2:25][CH2:24]3)=[O:22])[CH2:11]1)[CH2:17]2)(=[O:9])[NH2:7]

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acid2×HCID 66953610HCID 66953610, compound

Product 1

HCID 25065845HCID 25065845, compoundYield 7%

Procedure

To a solution of 2-(1′-((1-(3,5-dimethoxybenzylcarbamoyl)-4-adamantyloxy)carbonyl)-2,3-dihydrospiro[indene-1,4′-piperidine]-3-yl)acetic acid (40 mg, 0.096 mmol) was added 50% TFA (2.5 mL) at 0° C. The reaction mixture was stirred for 4 h at rt. The TFA was neutralized, and the solution was dried and concentrated to give crude product which was purified by preparative HPLC to give 2-(1′-((1-carbamoyl-4-adamantyloxy)carbonyl)-2,3-dihydrospiro[indene-1,4′-piperidine]-3-yl)acetic acid (2 mg, 7%). LC-MS Method 4 tR=2.078 min, m/z=467.2; 1H NMR: (400 MHz, CDCl3): δ=0.88 (m, 3H), 1.29 (m, 3H), 1.52-1.68 (m, 8H), 1.60-1.69 (m, 4H), 1.78-1.94 (m, 13H), 1.95-2.10 (m, 9H), 2.19-2.30 (m, 3H), 2.46 (m, 1H), 2.68 (m, 1H), 2.90-3.15 (m, 3H), 3.65 (m, 1H), 4.12-4.27 (m, 2H), 4.83-4.91 (m, 1H), 5.65-5.79 (m, 1H), 7.15-7.24 (m, 4H).

Workup

  1. customthe solution was dried
  2. concentrationconcentrated
  3. customto give crude product which
  4. customwas purified by preparative HPLC

Sources & evidence

ORD record
ord-ad9fb2d01c304aa890155107e5cfdfb5
Source dataset
uspto-grants-2015_01
Patent number
US08927715B2

Reaction notes

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