Sodium Hydroxide → HCID 54767998, compound

HRID 1503283Notes

Reaction equation

C([O:3][C:4](=[O:37])[CH:5]([NH:29][C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[CH2:6][C:7]1[C:15]2[C:10](=[CH:11][C:12]([C:16]3[CH:21]=[CH:20][C:19]([O:22][C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)=[CH:18][CH:17]=3)=[CH:13][CH:14]=2)[NH:9][CH:8]=1)C.[OH-].[Na+]>>[C:33]([O:32][C:30]([NH:29][CH:5]([CH2:6][C:7]1[C:15]2[C:10](=[CH:11][C:12]([C:16]3[CH:17]=[CH:18][C:19]([O:22][C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)=[CH:20][CH:21]=3)=[CH:13][CH:14]=2)[NH:9][CH:8]=1)[C:4]([OH:37])=[O:3])=[O:31])([CH3:36])([CH3:34])[CH3:35]

Participants

Reactant 2

HCID 14798Sodium Hydroxide

HCID 54765597HCID 54765597, compound

Product 1

HCID 54767998HCID 54767998, compoundYield 53%

Conditions

Temperature: 30 °C

Procedure

2-tert-Butoxycarbonylamino-3-[6-(4-phenoxyphenyl)-1H-indol-3-yl]-propionic acid (17) was prepared as follows: A mixture of compound 16 (0.1 g in 4 mL MeOH) and NaOH (0.5N aqueous, 0.5 mL) was shaken at 30° C. for 24 hours. The solvent was removed under vacuum. The residue was suspended in CHCl3 (20 mL), neutralized with 0.5N HCl to ˜pH 2, and concentrated to get compound 17 as a white solid (50 mg, 53%): 1H-NMR (400 MHz, CD3OD/CDCl3 3/1) δ: 7.8-7.84 (m, 3H), 7.75 (s, 1H), 747-7.57 (m, 3H), 7.2-7.32 (m, 6H), 4.61-4.65 (m, 1H), 3.51-3.55 (m, 1H), 3.31-3.37 (m, 1H), 1.43-1.6 (m, 9H); LC/MS: m/z=495.6 [M+Na+]+ (Calc: 472.5).

Workup

custom2-tert-Butoxycarbonylamino-3-[6-(4-phenoxyphenyl)-1H-indol-3-yl]-propionic acid (17) was prepared
customThe solvent was removed under vacuum
concentrationconcentrated

Sources & evidence

ORD record: ord-465a1480a0b64c0ea6c0e55e3b96dbfa
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09212139B2

Reaction notes

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