Potassium Carbonate → HCID 68858769, compound

HRID 1784235Notes

Reaction equation

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

Participants

Reactant 3

HCID 11430Potassium Carbonate

HCID 878361-(Bromomethyl)-4-(1,1-dimethylethyl)benzene

HCID 7019130Boc-Tyr-OMe

Product 1

HCID 68858769HCID 68858769, compoundYield 46.9%

Procedure

(S)-2-Tert-butoxycarbonylamino-3-[4-(4-tert-butyl-benzyloxy)-phenyl]-propionic acid methyl ester (290 mg) was prepared from (S)-2-tert-butoxycarbonylamino-3-(4-hydroxy-phenyl)-propionic acid methyl ester (425 mg, 1.4 mmol) and 4-tert-butylbenzyl bromide (1.6 mmol) with K2CO3 (398 mg, 2.9 mmol) as described in Procedure H and purified over silica gel (8:2, DCM-hexanes).

Workup

custompurified over silica gel (8:2, DCM-hexanes)

Sources & evidence

ORD record: ord-e5d7414a5d9c457a8edcfadd5d7db4b6
Source dataset: uspto-grants-2009_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07501538B2

Reaction notes

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