Sodium Carbonate → HCID 69108703, compound

HRID 1921678Notes

Reaction equation

HRID 1921678 reaction equation
C(=O)([O-])[O-].[Na+].[Na+].[CH3:7][C:8]1([CH:13]2[CH2:18][CH2:17][CH:16]([NH2:19])[CH2:15][CH2:14]2)[O:12][CH2:11][CH2:10][O:9]1.[C:20](Cl)([O:22][CH2:23][CH:24]1[C:36]2[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=2)[C:30]2[C:25]1=[CH:26][CH:27]=[CH:28][CH:29]=2)=[O:21]>O.O1CCOCC1>[CH:35]1[C:36]2[CH:24]([CH2:23][O:22][C:20](=[O:21])[NH:19][CH:16]3[CH2:17][CH2:18][CH:13]([C:8]4([CH3:7])[O:9][CH2:10][CH2:11][O:12]4)[CH2:14][CH2:15]3)[C:25]3[C:30](=[CH:29][CH:28]=[CH:27][CH:26]=3)[C:31]=2[CH:32]=[CH:33][CH:34]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 343679-Fluorenylmethyl chloroformateHCID 67491648HCID 67491648, compound

Product 1

HCID 69108703HCID 69108703, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of 12.72 g (120 mmol) of sodium carbonate is placed in 120 mL of water and combined with a solution of 7.00 g (38 mmol) of 4-(2-methyl-[1,3]dioxolan-2-yl)cyclohexylamine (cis/trans mixture) in 50 g of dioxane. After cooling to 0° C., a solution of 10.09 g (39 mmol) of Fmoc-chloride in 100 g of dioxane is added dropwise within 0.2 hours. The reaction mixture is stirred for 16 hours with the cooling removed. Then the mixture is poured onto water and extracted with ethyl acetate. The organic phase is washed with water, dried, and evaporated to dryness. The residue is purified by chromatography. Yield: 13.10 g (85%) cis/trans ratio 4:1; NMR: LH201618.

Workup

  1. customremoved
  2. additionThen the mixture is poured onto water
  3. extractionextracted with ethyl acetate
  4. washThe organic phase is washed with water
  5. customdried
  6. customevaporated to dryness
  7. customThe residue is purified by chromatography

Sources & evidence

ORD record
ord-afaaaa9d58d24b7f9943ec538ae0a964
Source dataset
uspto-grants-2012_05
Patent number
US08173699B2

Reaction notes

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