Diethyl Ether → Trp-OBn.TFA

HRID 1061087Notes

Reaction equation

HRID 1061087 reaction equation
[CH2:1]([O:8][C:9](=[O:29])[C@H:10]([CH2:19][C:20]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[NH:22][CH:21]=1)[NH:11]C(OC(C)(C)C)=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CCOCC.[C:35]([OH:41])([C:37]([F:40])([F:39])[F:38])=[O:36]>C(Cl)Cl>[NH2:11][C@H:10]([C:9]([O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[O:29])[CH2:19][C:20]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[NH:22][CH:21]=1.[F:38][C:37]([C:35]([OH:41])=[O:36])([F:40])[F:39]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 6422Trifluoroacetic acidHCID 10318477Boc-trp-obzl

Product 1

HCID 67691340Trp-OBn.TFA

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N-Boc-L-tryptophan benzyl ester (0.5 g, 1.27 mmol) was dissolved in a solution of 20% TFA in CH2Cl2. The reaction mixture was stirred under nitrogen at room temperature for 30 min and evaporated to dryness. Trituration of the resulting oil with Et2O provided 7 as a white solid (quantitative yield). mp=143-145° C.; 1H NMR (CD3CN) 9.42 (br s, 1H), 7.51 (d, J=8.0 Hz, 1H), 7.43 (d, J=8.2 Hz, 1H), 7.35 (m, 3H), 7.26 (m, 2H), 7.16 (m, 2H), 7.04 (t, J=7.9 Hz, 1H), 5.15 (d, J=12.3 Hz, 1H), 5.09 (d, J=12.3 Hz, 1H), 4.36 (t, J=6.2 Hz, 1H), 3.44 (d, J=6.2 Hz, 2H) ppm; 13C NMR (CDCl3) 170.1, 137.6, 136.0, 129.5, 129.4, 129.3, 128.1, 126.2, 122.9, 120.3, 119.1, 112.6, 107.5, 68.8, 54.4, 26.9 ppm; IR (KBr) 3412, 2840, 1742, 1673, 1498, 1205, 1137, 735 cm−1; HRMS calcd for C18H19N2O2 294.1368 found 294.1362.

Workup

  1. customevaporated to dryness

Sources & evidence

ORD record
ord-8300b6dc7f3d462893cf46700176386c
Source dataset
uspto-grants-2003_02
Patent number
US06525154B1

Reaction notes

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