Trifluoroacetic acid → O-allyl L-seryl glycine methyl ester trifluoroacetate

HRID 2370902Notes

Reaction equation

HRID 2370902 reaction equation
[CH3:1][O:2][C:3](=[O:22])[CH2:4][NH:5][C:6](=[O:21])[C@H:7]([CH2:16][O:17][CH2:18][CH:19]=[CH2:20])[NH:8]C(OC(C)(C)C)=O.[C:23]([OH:29])([C:25]([F:28])([F:27])[F:26])=[O:24]>C(Cl)Cl>[F:26][C:25]([F:28])([F:27])[C:23]([OH:29])=[O:24].[CH3:1][O:2][C:3](=[O:22])[CH2:4][NH:5][C:6](=[O:21])[C@H:7]([CH2:16][O:17][CH2:18][CH:19]=[CH2:20])[NH2:8]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acid2×HCID 86671356N-tert-butoxycarbonyl O-allyl L-seryl glycine methyl ester

Product 1

HCID 86671357O-allyl L-seryl glycine methyl ester trifluoroacetate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N-tert-butoxycarbonyl O-allyl L-seryl glycine methyl ester 18 (5.86 g, 18.3 mmol) was dissolved in CH2Cl2 (30 mL) and TFA (30 mL) added at room temperature. The reaction mixture was stirred for 2 hours before the solvent and bulk of excess TFA were evaporated affording a brownish liquid (7.50 g). The residue was washed with Et2O (2×25 mL), redissolved in CH2Cl2 (25 mL), the solvents evaporated and the residue dried under reduced pressure affording a brownish, viscous liquid (6.01 g, 98%); δH (300 MHz; d6-DMSO) 9.02 (1H, t, J 6, NH), 8.33 (3H, br s, NH3+), 5.87 (1H, ddt, J 5, 10 and 17, CH═CH2), 5.29 (1H, ddt, J 1, 2 and 17, CH═CHH), 5.21-5.14 (1H, m, CH═CHH), 4.10 (1H, m, CαH(Ser(All))), 4.00 (2H, ddd, J 1, 1 and 5, CH2CH═CH2), 3.95 (2H, d, J 6, CαH2(Gly)), 3.78-3.67 (2H, m, CH2), 3.64 (3H, s, OCH3); δC (75 MHz; d6-DMSO) 169.7, 167.0, 158.4 (q, JCF 32), 134.4, 116.7 (q, JCF 296), 71.4, 68.0, 54.9, 52.3, 51.8, 40.7; m/z (ESI) 217.1194 (M+; C9H17N2O4 requires 217.1188)

Workup

  1. customwere evaporated

Sources & evidence

ORD record
ord-8657e65f89aa4666b880ece0421a3b47
Source dataset
uspto-grants-2014_04
Patent number
US08710008B2

Reaction notes

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