Water → HCID 25066065, compound

HRID 1424625Notes

Reaction equation

HRID 1424625 reaction equation
C[O:2][C:3](=[O:29])[CH2:4][CH:5]1[CH2:28][CH2:27][C:8]2([CH2:13][CH2:12][N:11]([C:14]([O:16][CH:17]3[CH:24]4[CH2:25][CH:20]5[CH2:21][CH:22]([CH2:26][CH:18]3[CH2:19]5)[CH2:23]4)=[O:15])[CH2:10][CH2:9]2)[CH2:7][CH2:6]1.O.O[Li].O.C(O)(C(F)(F)F)=O>C1COCC1.C(O)(=O)C.CO>[CH:18]12[CH2:26][CH:22]3[CH2:21][CH:20]([CH2:25][CH:24]([CH2:23]3)[CH:17]1[O:16][C:14]([N:11]1[CH2:10][CH2:9][C:8]3([CH2:27][CH2:28][CH:5]([CH2:4][C:3]([OH:29])=[O:2])[CH2:6][CH2:7]3)[CH2:13][CH2:12]1)=[O:15])[CH2:19]2

Participants

8

Reactant 4

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 168937Lithium hydroxide, monohydrateHCID 25066064HCID 25066064, compound

Product 1

HCID 25066065HCID 25066065, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

(2-Adamantyl) 9-(2-methoxy-2-oxoethyl)-3-azaspiro[5.5]undecane-3-carboxylate (30 mg, 74 μmol) was dissolved in THF (0.25 mL), water (0.25 mL) and MeOH (0.5 mL) and LiOH.H2O (8 mg, 0.19 mmol) was added. The mixture was stirred at rt for 2 d and TFA (10 mL, 0.14 mmol) was added. The solution was submitted directly to prep HPLC to afford 2-(34(2-adamantyl)oxycarbonyl)-3-azaspiro[5.5]undecan-9-yl)acetic acid (10.5 mg, 36%). LC-MS Method 1 tR=2.17 min, m/z=390; 1H NMR (CDCl3) δ=1.0-2.05 (27H), 2.27 (d, 2H), 3.44 (m, 4H), 4.83 (s, 1H).

Sources & evidence

ORD record
ord-34616527e1934e8eb81e43e4490aa135
Source dataset
uspto-grants-2015_01
Patent number
US08927715B2

Reaction notes

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