Trityl chloride → N-(Triphenylmethyl)-L-serine methyl ester

HRID 1425687Notes

Reaction equation

Cl.[CH3:2][O:3][C:4](=[O:9])[C@H:5]([CH2:7][OH:8])[NH2:6].CCN(CC)CC.Cl[C:18]([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>>[OH:8][CH2:7][C@H:5]([NH:6][C:18]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)([C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1)[C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1)[C:4]([O:3][CH3:2])=[O:9]

Participants

Reactant 3

HCID 6456Trityl chloride

HCID 8471Triethylamine

HCID 2723730L-Serine, methyl ester, hydrochloride (1:1)

Product 1

HCID 7128367N-(Triphenylmethyl)-L-serine methyl esterYield 94%

Procedure

(U. Larsson and R. Carlson, Acta Chem. Scand. 1994, 48, 511-516; M. Meyer et al., J. Am. Chem. Soc. 1997, 119, 10093-10103). Using the preceding procedure and using L-serine methyl ester hydrochloride (20.00 g, 0.13 mol), Et3N (35.82 mL, 0.26 mol) and TrCl (36.53 g, 0.13 mol) gave 43.80 g (94%) of crude desired product as a pale yellow crystalline solid: Rf=0.50 (1/1 EtOAc/hexanes); 1H NMR (CDCl3) δ 2.31 (br s, 1H), 2.84-3.02 (br m, 1H), 3.29 (s, OCH3), 3.50-3.59 (m, CHH′OH, CH), 3.63-3.74 (m, CHH′OH), 7.18-7.29 (m, 9 PhH), 7.48-7.50 (m, 6 PhH).

Sources & evidence

ORD record: ord-da764867302e45889599af6fd57cc477
Source dataset: uspto-grants-2015_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08933065B2

Reaction notes

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