Diethyl Ether → HCID 66862433, compound

HRID 254794Notes

Reaction equation

HRID 254794 reaction equation
[N:1]([C@@H:4]1[C@@H:10]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=2)[C@H:9]([O:21][CH2:22][C:23]2[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=2)[C@@H:8]([CH2:31][O:32][CH2:33][C:34]2[CH:39]=[CH:38][C:37]([O:40][CH3:41])=[CH:36][CH:35]=2)[O:7][CH:5]1[OH:6])=[N+]=[N-].SC[C@H]([C@@H](CS)O)O.C(N(CC)CC)C.C(OCC)C>CN(C=O)C.C(OCC)(=O)C>[NH2:1][C@@H:4]1[C@@H:10]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=2)[C@H:9]([O:21][CH2:22][C:23]2[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=2)[C@@H:8]([CH2:31][O:32][CH2:33][C:34]2[CH:35]=[CH:36][C:37]([O:40][CH3:41])=[CH:38][CH:39]=2)[O:7][CH:5]1[OH:6]

Participants

7

Reactant 4

HCID 3283Diethyl EtherHCID 8471TriethylamineHCID 446094D-1,4-DithiothreitolHCID 91184934HCID 91184934, compound

Product 1

HCID 66862433HCID 66862433, compoundYield 69%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of the azide 63 (110.2 mmol) in dry DMF (275 mL) was added dithiothreitol (220.4 mmol). The reaction mixture was then degassed with a stream of nitrogen, cooled to 0 C, and triethylamine (220.4 mmol) added. The solution was then allowed to return to room temperature and subsequently stirred for 24 h. The solution was then diluted with ethyl acetate and washed with water, brine, dried (MgSO4), the solvents removed in vacuo, and resulting residue treated with diethyl ether (˜250 mL) to give the desired product 64 as a white solid (69%), LCMS [M+H]+=540.25.

Workup

  1. customThe reaction mixture was then degassed with a stream of nitrogen
  2. additionadded
  3. customto return to room temperature
  4. washwashed with water, brine
  5. dry with materialdried (MgSO4)
  6. customthe solvents removed in vacuo
  7. customresulting residue

Sources & evidence

ORD record
ord-9f2cc9cac27d4f53a42da7ff9971e834
Source dataset
uspto-grants-2011_01
Patent number
US07875707B2

Reaction notes

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