Tetrahydrofuran → HCID 22102332, compound

HRID 1457244Notes

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 a-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-fb1f841ac9ff4dea9cad4156f35d7747
Source dataset: uspto-grants-1998_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05846942

Reaction notes

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