Water → HCID 89569084, compound

HRID 578747Notes

Reaction equation

HRID 578747 reaction equation
[S:1](Cl)([CH3:4])(=[O:3])=[O:2].[C:6]1([CH:12]2[O:19][CH2:18][C@H:17]3[C@:15]([CH2:20][OH:21])([CH2:16]3)[CH2:14][O:13]2)[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.C(N(CC)CC)C.O>ClCCl>[CH3:4][S:1]([O:21][CH2:20][C@:15]12[CH2:16][C@H:17]1[CH2:18][O:19][CH:12]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[O:13][CH2:14]2)(=[O:3])=[O:2]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 71570849HCID 71570849, compound

Product 1

HCID 89569084HCID 89569084, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

In a reactor, a solution of mesyl chloride (280 g, 2.4 mol) in dichloromethane (2 L) was added to a mixture of [(1S,7R)-4-phenyl-3,5-dioxabicyclo[5.1.0]octan-1-yl]methanol (450 g, 2.0 mol) and triethylamine (310 g, 3.1 mol) in dichloromethane (4.7 L). A maximum internal temperature of 27° C. was observed. The mixture was stirred for 1 hour. Water (4.5 L) was added, phases were separated and the aqueous phase was extracted with dichloromethane (2.3 L). The combined organic phases were washed with water (2.3 L) and subsequently concentrated under reduced pressure yielding off-white solid product. This material was used as such in the next reaction step without further purification.

Workup

  1. customA maximum internal temperature of 27° C.
  2. customphases were separated
  3. extractionthe aqueous phase was extracted with dichloromethane (2.3 L)
  4. washThe combined organic phases were washed with water (2.3 L)
  5. concentrationsubsequently concentrated under reduced pressure
  6. customyielding off-white solid product
  7. customsuch in the next reaction step
  8. customwithout further purification

Sources & evidence

ORD record
ord-204df2cfd0414ad18f946a8ffa869abc
Source dataset
uspto-grants-2015_05
Patent number
US09040699B2

Reaction notes

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