Diethyl Ether → HCID 67085753, compound

HRID 1874619Notes

Reaction equation

HRID 1874619 reaction equation
[C:1]([O:4][CH2:5][C@H:6]([NH:20]C(OC(C)(C)C)=O)[C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:14][CH:15]([CH3:19])[CH2:16][CH2:17][CH3:18])=[CH:9][CH:8]=1)(=[O:3])[CH3:2].CCOCC>Cl>[C:1]([O:4][CH2:5][C@H:6]([NH2:20])[C:7]1[CH:8]=[CH:9][C:10]([O:13][CH2:14][CH:15]([CH3:19])[CH2:16][CH2:17][CH3:18])=[CH:11][CH:12]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 3283Diethyl EtherHCID 67086154(2R)-2-(t-butoxycarbonylamino)-2-(4-(2-methylpentyloxy)phenyl)ethyl acetate

Product 1

HCID 67085753HCID 67085753, compound

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A solution of (2R)-2-(t-butoxycarbonylamino)-2-(4-(2-methylpentyloxy)phenyl)ethyl acetate (5.50 g, 14.49 mmol) in 2 M HCl in ether (72.5 mL, 144.9 mmol) was stirred at room temperature for 12 h. The precipitate formed was collected on a Buchner funnel, washed with ether, and dried under vacuum to afford (2R)-2-amino-2-(4-(2-methylpentyloxy)phenyl)ethyl acetate.HCl (3.70 g, 81% yield) as a tan solid: 1H NMR (400 MHz, DMSO-d6) δ 8.80 (br. s., 3 H), 7.46 (d, J=8.8 Hz, 2H), 6.98 (d, J=8.8 Hz, 2H), 4.43-4.55 (m, 1H), 4.25-4.37 (m, 2H), 3.84 (dd, J=9.6, 6.0 Hz, 1H), 3.74 (dd, J=9.6, 6.8 Hz, 1H), 2.05 (s, 3H), 1.81-1.93 (m, 1H), 1.25-1.49 (m, 3H), 1.10-1.23 (m, 1H), 0.96 (d, J=6.5 Hz, 3H), 0.88 (t, J=7.1 Hz, 3H); LRMS (ESI) m/e 280.4 [(M+H)+, calcd for C16H26NO3 280.2].

Workup

  1. customThe precipitate formed
  2. customwas collected on a Buchner funnel
  3. washwashed with ether
  4. customdried under vacuum

Sources & evidence

ORD record
ord-cc723b681c994b689c018670850f924d
Source dataset
uspto-grants-2012_11
Patent number
US08304577B2

Reaction notes

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