Benzenesulfonyl chloride → HCID 19003155, compound

HRID 2259292Notes

Reaction equation

HRID 2259292 reaction equation
Cl.[NH2:2][CH:3]([CH2:16][C:17]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[NH:19][CH:18]=1)[C:4]([O:6][CH2:7][C:8]1[CH:13]=[C:12]([CH3:14])[CH:11]=[C:10]([CH3:15])[CH:9]=1)=[O:5].C(N(CC)CC)C.[C:33]1([S:39](Cl)(=[O:41])=[O:40])[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1>O1CCCC1>[C:33]1([S:39]([NH:2][CH:3]([CH2:16][C:17]2[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[NH:19][CH:18]=2)[C:4]([O:6][CH2:7][C:8]2[CH:9]=[C:10]([CH3:15])[CH:11]=[C:12]([CH3:14])[CH:13]=2)=[O:5])(=[O:41])=[O:40])[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1

Participants

5

Reactant 3

HCID 7369Benzenesulfonyl chlorideHCID 8471TriethylamineHCID 19003122HCID 19003122, compound

Product 1

HCID 19003155HCID 19003155, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3,5-Dimethylbenzyl 2-amino-3-(3-indolyl)propionate hydrochloride (1.0 g) was suspended in tetrahydrofuran (10 ml). Triethylamine (0.38 ml) was added and the solution was stirred for 15 mins. Benzenesulphonyl chloride (0.35 ml) was added and the solution was stirred at room temperature for 1 hour. Work-up as for Example 14 gave a solid which was recrystallised from ethanol to yield the title compound, 0.85 g, m.p. 114°-116° C. 1H NMR (360 MHz, CDCl3) δ7.98 (1H, s), 7.72 (2H, d, J=7 Hz), 7.54-7.30 (5H, m), 7.17 (1H, t, J=7 Hz), 7.06 (1H, t. J=7 Hz), 6.94 (1H, s), 6.89 (1H, s), 6.62 (2H, s), 5.17 (1H, d, J=9.2 Hz), 4.68 (2H, ABq, J=11.9 Hz), 4.33 (1H, m), 3.27 (2H, m), 2.27 (6H, s).

Workup

  1. stirringthe solution was stirred at room temperature for 1 hour
  2. customgave a solid which
  3. customwas recrystallised from ethanol

Sources & evidence

ORD record
ord-d9d279ba5e164a6bb0650b5b104ff0e4
Source dataset
uspto-grants-1995_12
Patent number
US05472978

Reaction notes

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