2-(Chloromethyl)anisole → HCID 19003118, compound

HRID 2259284Notes

Reaction equation

HRID 2259284 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][CH:8]=[CH:7][C:4]=1[CH2:5]Cl.[C:11]([NH:18][C@H:19]([C:30]([OH:32])=[O:31])[CH2:20][C:21]1[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[NH:23][CH:22]=1)([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12]>>[CH3:16][C:14]([CH3:17])([O:13][C:11]([NH:18][CH:19]([CH2:20][C:21]1[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[NH:23][CH:22]=1)[C:30]([O:32][CH2:5][C:4]1[CH:7]=[CH:8][CH:9]=[CH:10][C:3]=1[O:2][CH3:1])=[O:31])=[O:12])[CH3:15]

Participants

3

Reactant 2

HCID 814952-(Chloromethyl)anisoleHCID 83169N-tert-Butoxycarbonyl-L-tryptophan

Product 1

HCID 19003118HCID 19003118, compound

Procedure

Following the method of Example 1, 2-methoxybenzyl chloride (3.9) and N α BOC-L-tryptophan (7.6 g) gave the title compound which was recrystallised from ethyl acetate/petroleum ether (3.4 g), m.p. 132°-133° C. 1H NMR (360 MHz, CDCl3) δ7.99 (1H, s), 7.56 (1H, d, J=Hz), 7.33-7.07 (5H, m), 6.93-6.66 (3H, m), 5.21-5.07 (3H, m), 4.70-4.67 (1H, m), 3.01 (3H, s), 3.30 (1H, m), 1.41 (9H, s). Found: C, 67.91; H, 6.65; N, 6.60; C24H28N2O5 requires C, 68.00; H, 6.70; N, 6.66%.

Sources & evidence

ORD record
ord-a0063a7eef09462c8c894dd49ba9a0fa
Source dataset
uspto-grants-1995_12
Patent number
US05472978

Reaction notes

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