Triethylamine → 2,3,4,6-Tetra-o-acetyl-n-[({2-(r/s)-[(tert-butoxycarbonyl)amino]-dodecyl}amino)-carbonothioyl]-beta-d-glucopyranosylamine

HRID 970303Notes

Reaction equation

HRID 970303 reaction equation
[C:1]([O:4][C@@H:5]1[C@@H:10]([O:11][C:12](=[O:14])[CH3:13])[C@H:9]([O:15][C:16](=[O:18])[CH3:17])[C@@H:8]([CH2:19][O:20][C:21](=[O:23])[CH3:22])[O:7][C@H:6]1[N:24]=[C:25]=[S:26])(=[O:3])[CH3:2].[NH2:27][CH2:28][CH:29]([NH:40][C:41](=[O:47])[O:42][C:43]([CH3:46])([CH3:45])[CH3:44])[CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH3:39].C(N(CC)CC)C>C(Cl)Cl>[C:1]([O:4][C@@H:5]1[C@@H:10]([O:11][C:12](=[O:14])[CH3:13])[C@H:9]([O:15][C:16](=[O:18])[CH3:17])[C@@H:8]([CH2:19][O:20][C:21](=[O:23])[CH3:22])[O:7][C@H:6]1[NH:24][C:25]([NH:27][CH2:28][CH:29]([NH:40][C:41]([O:42][C:43]([CH3:44])([CH3:46])[CH3:45])=[O:47])[CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH3:39])=[S:26])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 994622,3,4,6-Tetra-O-acetylglucopyranosylisothiocyanateHCID 87843007t-butyl N-(1-aminododecan-2-yl) carbamate

Product 1

HCID 878429672,3,4,6-Tetra-o-acetyl-n-[({2-(r/s)-[(tert-butoxycarbonyl)amino]-dodecyl}amino)-carbonothioyl]-beta-d-glucopyranosylamineYield 98.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl isothiocyanate 37 (25.0 mg, 0.0617 mmol), tert-butyl N-[1-(R/S)-(aminomethyl)-undecyl]carbamate (27.8 mg, 0.0927 mmol) and triethylamine (12.5 mg, 0.0124 mmol) were dissolved in abs. CH2Cl2 (5 ml) and stirred at room temperature for 1 hour. Following evaporation, the residue was purified by column chromatography to give 65 (42.0 mg, 94%)

Workup

  1. customevaporation
  2. customthe residue was purified by column chromatography

Sources & evidence

ORD record
ord-4e89b05a51ef4760917d6a4937acadfe
Source dataset
uspto-grants-2007_12
Patent number
US07312194B2

Reaction notes

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