Dicyclohexylamine → HCID 67411810, compound

HRID 909196Notes

Reaction equation

HRID 909196 reaction equation
[C:1]([O:5][C:6]([C@@H:8]([CH2:12][CH2:13][OH:14])[C:9]([OH:11])=[O:10])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH:15]1([NH:21][CH:22]2[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]2)[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1>CCO>[C:1]([O:5][C:6]([C@@H:8]([CH2:12][CH2:13][OH:14])[C:9]([OH:11])=[O:10])=[O:7])([CH3:3])([CH3:4])[CH3:2].[CH:22]1([NH:21][CH:15]2[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20]2)[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27]1

Participants

4

Reactant 2

HCID 7582DicyclohexylamineHCID 67411811HCID 67411811, compound

Product 1

HCID 67411810HCID 67411810, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of (S)-2-(tert-butoxycarbonyl)-4-hydroxybutanoic acid (72.6 g, 331 mmol) in EtOH (500 mL) was added dropwise dicyclohexylamine (73 mL, 364 mmol). The mixture was stirred for 2 hours at room temperature and then concentrated under reduced pressure. The white solid was dried under high vacuum and then triturated with ether (1000 mL). The fine white powder was collected by filtration, washed with ether and dried under high vacuum (125.6 g, 95% yield).

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe white solid was dried under high vacuum
  3. customtriturated with ether (1000 mL)
  4. filtrationThe fine white powder was collected by filtration
  5. washwashed with ether
  6. customdried under high vacuum (125.6 g, 95% yield)

Sources & evidence

ORD record
ord-ca7e4f50802e4203addf372675d7b48d
Source dataset
uspto-grants-2011_09
Patent number
US08017641B2

Reaction notes

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