Triethylamine → (2S,3R,4R,5S)-2,5-Bis-(N-Cbz-amino)-3,4-bis-(mesyloxy)-1,6-diphenylhexane

HRID 235502Notes

Reaction equation

HRID 235502 reaction equation
[C:1]([NH:11][C@H:12]([C@@H:20]([OH:42])[C@H:21]([OH:41])[C@@H:22]([NH:30][C:31]([O:33][CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)=[O:32])[CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2].[CH3:43][S:44](Cl)(=[O:46])=[O:45].C(N(CC)CC)C>ClCCl.CN(C)C1C=CN=CC=1>[C:1]([NH:11][C@H:12]([C@@H:20]([O:42][S:44]([CH3:43])(=[O:46])=[O:45])[C@H:21]([O:41][S:44]([CH3:43])(=[O:46])=[O:45])[C@@H:22]([NH:30][C:31]([O:33][CH2:34][C:35]1[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=1)=[O:32])[CH2:23][C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1)[CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 10393187dibenzyl ((2S,3R,4R,5S)-3,4-dihydroxy-1,6-diphenylhexane-2,5-diyl)dicarbamate

Product 1

HCID 18655486(2S,3R,4R,5S)-2,5-Bis-(N-Cbz-amino)-3,4-bis-(mesyloxy)-1,6-diphenylhexaneYield 90%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

A slurry of 1.50 g (2.64 mmol) of (2S,3R,4R,5S)-2,5-bis-(N-Cbz-amino)-3,4-dihydroxy-1,6-diphenylhexane in 50 ml of anhydrous dichloromethane was cooled to 0° C. and treated sequentially with 0.43 ml of methanesulfonyl chloride, 64 mg of 4-dimethylaminopyridine and 1.1 ml of triethylamine. The resulting mixture was stirred for 15 h with the temperature being allowed to slowly climb to ambient temperature. After treatment with aqueous NH4Cl, the separated organic layer was washed with aqueous NaHCO3, dried over MgSO4, and concentrated in vacuo to provide 1.70 g (90%) of the desired compound, m.p. 153°-155° C. 1H NMR (CDCl3) δ 2.73 (m, 2H), 2.92 (m, 2H), 3.09 (s, 6H), 4.61 (m, 2H), 4.83-5.06 (m, 8H), 7.12-7.37 (m, 20H).

Workup

  1. customto slowly climb to ambient temperature
  2. washAfter treatment with aqueous NH4Cl, the separated organic layer was washed with aqueous NaHCO3
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ff8740a4013e4e29901e2c60ff7bea4a
Source dataset
uspto-grants-1997_01
Patent number
US05597926

Reaction notes

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