4-Methoxyphenol → HCID 12179184, compound

HRID 1165391Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:14]=[CH:13][C:6](C[C@@H](C([O-])=O)N)=[CH:5][CH:4]=1.[CH2:15]([O:22][C:23]([NH:25][C@H:26]([C:28]([OH:30])=[O:29])[CH3:27])=[O:24])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.COC1C=CC(O)=CC=1.C1(N=C=NC2CCCCC2)CCCCC1>>[CH3:1][O:2][C:3]1[CH:14]=[CH:13][C:6]([O:29][C:28](=[O:30])[C@H:26]([CH3:27])[NH:25][C:23]([O:22][CH2:15][C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)=[O:24])=[CH:5][CH:4]=1

Participants

Reactant 4

HCID 90154-Methoxyphenol

HCID 10868Dicyclohexylcarbodiimide

HCID 736104N-carbobenzyloxyalanine

HCID 86743808HCID 86743808, compound

Product 1

HCID 12179184HCID 12179184, compoundYield 57%

Procedure

4-Methoxyphenylalaninate was first prepared by reacting N-benzyloxycarbonyl-(S)-alanine (10.9 g, 0.049 mole) with 4-methoxyphenol and 1,3-dicyclohexylcarbodiimide to give 9.2 g (57%) of N-benzyloxycarbonyl-(S)-alanine 4-methoxyphenyl ester, mp 128°-129° C.; [α]D25 -18.98° (c=0.769, CHCl3); IR (KBr): 3320, 1750 and 1660 cm-1 ; NMR (δ): 1.52 (3H, d, J=7.4 Hz), 3.72 (3H, s), 4.48 (1H, q, J=7.4 Hz), 5.08 (2H, s), 5.36-5.48 (1H, broad, signal disappeared in D2O), 6.68-7.48 (9H, m). Anal. for C18H19NO5 : Calcd: C, 65.65; H, 5,77; N, 4.25. Found: C, 65.74; H, 5.91; N, 4.31.

Sources & evidence

ORD record: ord-4f81ad9b8bc343968eb793c8fc026305
Source dataset: uspto-grants-1990_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04909935

Reaction notes

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