Hydrochloric Acid → HCID 67438259, compound

HRID 1874648Notes

Reaction equation

HRID 1874648 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C@@H:15]([NH:28][C:29](=[O:38])[C@H:30]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[CH3:31])[C@@H:16]2[CH2:20][CH2:19][CH2:18][N:17]2C(OC(C)(C)C)=O)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl>>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C@H:15]([C@H:16]2[CH2:20][CH2:19][CH2:18][NH:17]2)[NH:28][C:29](=[O:38])[C@H:30]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[CH3:31])=[CH:11][CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 67439472HCID 67439472, compound

Product 1

HCID 67438259HCID 67438259, compoundYield 61.9%

Procedure

A solution of (S)-tert-butyl 2-((R)-(4-(benzyloxy)phenyl)((S)-2-phenylpropanamido)methyl)pyrrolidine-1-carboxylate (386 mg, 0.750 mmol) in HCl (2M in diethyl ether) (3.750 mL, 7.50 mmol) was stirred at room temperature for 4 h, then concentrated in vacuo. The residue was purified by HPLC (50% methanol/water with 0.1% TFA) to afford (S)-N-((R)-(4-(benzyloxy)phenyl)((R)-pyrrolidin-2-yl)methyl)-2-phenylpropanamide (14.7 mg, 0.034 mmol, 61.9% yield) as a slightly yellow oil. 1H NMR (400 MHz, CDCl3) δ 7.23-7.43 (m, 11H), 6.94 (d, J=8.56 Hz, 2H), 6.81 (d, J=8.81 Hz, 2H), 6.64 (d, J=5.79 Hz, 1H), 4.99 (s, 1H), 4.79 (dd, J=8.18, 3.15 Hz, 1H), 3.67 (q, J=7.22 Hz, 1H), 3.31 (td, J=7.68, 3.27 Hz, 1H), 2.72 (td, J=6.67, 2.27 Hz, 1H), 1.72-1.84 (m, 2H), 1.60 (td, J=13.28, 6.17 Hz, 2H), 1.48-1.55 (m, 4H), 1.33-1.45 (m, 1H); LRMS (ESI) m/e 415.40 [(M+H)+, calcd for C27H31N2O2 415.24].

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue was purified by HPLC (50% methanol/water with 0.1% TFA)

Sources & evidence

ORD record
ord-db2671d04668400d858cdd92e08875de
Source dataset
uspto-grants-2012_11
Patent number
US08304577B2

Reaction notes

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