Tetrahydrofuran → HCID 22102332, compound

HRID 233632Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:17])[C:4]([CH3:16])([CH2:6][C:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[NH:9][CH:8]=1)[NH2:5].C(N([CH2:23][CH3:24])CC)C.[CH2:25]1[CH2:29][O:28][CH2:27][CH2:26]1>>[CH3:1][O:2][C:3](=[O:17])[C:4]([CH3:16])([CH2:6][C:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[NH:9][CH:8]=1)[NH:5][C:29]([CH2:25][C:26]1([C:24]2[CH:23]=[CH:7][CH:6]=[CH:4][CH:3]=2)[CH2:15][CH2:10][CH2:11][CH2:27]1)=[O:28]

Participants

Reactant 3

HCID 8028Tetrahydrofuran2×

HCID 8471Triethylamine

HCID 2795140Methyl alpha-methyltryptophanate

Product 1

HCID 22102332HCID 22102332, compoundYield 90%

Procedure

To a stirred solution of 1-phenyl 1-cyclopentyl methylchloroformate (0.65 g, 2.75 mmol) in dry THF (10 mL) was added a solution of α-methyl-DL-tryptophan methyl ester (0.60 g, 2.5 mmol) followed by triethylamine (0.5 g, 5.0 mmol) in dry THF. The reaction mixture was stirred for 30 minutes and then filtered, concentrated and chromatographed to give an oil (0.9 g, 90%). 1H NMR (200 MHz, CDCl3) δ 8.0 (1H, br s), 7.50 (1H, d, J 7 Hz), 7.40-7.0 (8H, m), 6.6 (1H, br s), 5.35 (1H, br s), 4.15 (2H, s), 3.65 (3H, s), 3.6-3.0 (2H, m), 2.10-1.85 (4H, m), 1.85-1.60 (4H, m), 1.55 (3H, s).

Workup

filtrationfiltered
concentrationconcentrated
customchromatographed

Sources & evidence

ORD record: ord-27ef1a8ac4f14c878af434c051a9f9b0
Source dataset: uspto-grants-1997_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05593967

Reaction notes

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