Triethylamine → HCID 86606229, compound

HRID 1370989Notes

Reaction equation

[CH3:1][S:2](Cl)(=[O:4])=[O:3].[C:6]([O:10][C:11]([NH:13][CH2:14][CH2:15][CH2:16][CH2:17][N:18]([C:49]([O:51][C:52]([CH3:55])([CH3:54])[CH3:53])=[O:50])[CH2:19][CH:20]([CH:28]([CH2:37][CH2:38][CH2:39][CH2:40][NH:41][C:42]([O:44][C:45]([CH3:48])([CH3:47])[CH3:46])=[O:43])[NH:29][C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][OH:27])=[O:12])([CH3:9])([CH3:8])[CH3:7].C(N(CC)CC)C>ClCCl>[CH3:1][S:2]([O:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH:20]([CH:28]([CH2:37][CH2:38][CH2:39][CH2:40][NH:41][C:42]([O:44][C:45]([CH3:48])([CH3:47])[CH3:46])=[O:43])[NH:29][C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[CH2:19][N:18]([CH2:17][CH2:16][CH2:15][CH2:14][NH:13][C:11]([O:10][C:6]([CH3:7])([CH3:8])[CH3:9])=[O:12])[C:49]([O:51][C:52]([CH3:55])([CH3:54])[CH3:53])=[O:50])(=[O:4])=[O:3]

Participants

Conditions

Temperature: 0 °C

Procedure

Methanesulphonyl chloride (1.25 ml, 16.21 mmol) was added to a stirred solution of B6 (9.67 g, 13.5 mmol) in dry dichloromethane (100 ml) containing triethylamine (2.82 ml, 20.26 mmol) at 0° C. The flask was stirred at 0° C. for 1 hr, then overnight at room temperature. The solvent was removed and the residue chromatographed (silica—50% ethyl acetate in hexane) to yield the title compound (8.5 g, 79%. C38H74N4O11S requires 794. Found DCl: M++1, 795.6. δH (CDCl3) 3.45 (2H, t, CH2O), 2.9-3.3 (12H, m, CH2N), 2.99 (3H, s, MeS), 1.95 (1H, brm, CH2CH(CH2)2), 1.2-1.8 (50H, m, CH2).

Workup

customovernight
customat room temperature
customThe solvent was removed
customthe residue chromatographed (silica—50% ethyl acetate in hexane)

Sources & evidence

ORD record: ord-0a1d2ddb6e0442a4bf54732d4cf9365f
Source dataset: uspto-grants-2003_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06583301B1

Reaction notes

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