Hydrochloric Acid → HCID 178453557, compound

HRID 713901Notes

Reaction equation

[C:1]([O:5][C:6]([N:8]([CH2:16][C:17]1[CH:26]=[CH:25][C:24]2[C:19](=[CH:20][CH:21]=[C:22]([O:27][C@H:28]3[CH2:33][CH2:32][C@H:31]([C:34]([CH3:37])([CH3:36])[CH3:35])[CH2:30][CH2:29]3)[CH:23]=2)[CH:18]=1)[CH2:9][CH2:10][C:11]([O:13]CC)=[O:12])=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+].Cl>CCO>[C:1]([O:5][C:6]([N:8]([CH2:16][C:17]1[CH:26]=[CH:25][C:24]2[C:19](=[CH:20][CH:21]=[C:22]([O:27][C@H:28]3[CH2:29][CH2:30][C@H:31]([C:34]([CH3:37])([CH3:36])[CH3:35])[CH2:32][CH2:33]3)[CH:23]=2)[CH:18]=1)[CH2:9][CH2:10][C:11]([OH:13])=[O:12])=[O:7])([CH3:3])([CH3:4])[CH3:2]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of ethyl 3-(tert-butoxycarbonyl((6-((trans)-4-tert-butylcyclohexyloxy)naphthalen-2-yl)methyl)amino)propanoate (485 mg, 0.94 mmol) in EtOH (10 mL) was added aqueous NaOH (2 mL, 20%, 5.0 equiv) and refluxed for 2 h. Then the reaction was cooled to 0° C., the pH of the solution was adjusted to 6 using 1M HCl, concentrated and the residue was dissolved in DCM, washed with water, dried and concentrated to give 3-(tert-butoxycarbonyl((6-((trans)-4-tert-butylcyclohexyloxy)naphthalen-2-yl)methyl)amino)propanoic acid as a gray oil (392 mg, 75%). ESI-MS (M+H+): 484.3. 1H NMR (400 MHz, DMSO-d6) δ: 7.79˜7.72 (m, 2H), 7.62˜7.57 (m, 1H), 7.35˜7.26 (m, 2H), 7.14˜7.08 (m, 1H), 4.49 (s, 2H), 4.41˜4.30 (m, 1H), 3.38˜3.26 (m, 2H), 2.33˜2.26 (t, 2H), 2.23˜2.15 (m, 2H), 1.95˜1.84 (m, 2H), 1.47˜1.28 (m, 11H), 1.27˜1.15 (m, 2H), 1.11˜1.02 (m, 1H), 0.87 (s, 9H).

Workup

temperaturerefluxed for 2 h
concentrationconcentrated
dissolutionthe residue was dissolved in DCM
washwashed with water
customdried
concentrationconcentrated

Sources & evidence

ORD record: ord-46107b21da9d4041898a9bd4e03bfea5
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09186367B2

Reaction notes

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