Sodium Carbonate → HCID 46193050, compound

HRID 333030Notes

Reaction equation

HRID 333030 reaction equation
C(=O)([O-])[O-].[Na+].[Na+].[CH:7]1[C:19]2[CH:18]([CH2:20][O:21][C:22](Cl)=[O:23])[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11]=2[CH:10]=[CH:9][CH:8]=1.[Cl:25][C@H:26]1[CH2:30][NH:29][C@@H:28]2[C@@H:31]([OH:34])[CH2:32][O:33][C@H:27]12>O.O1CCOCC1>[Cl:25][C@H:26]1[CH2:30][N:29]([C:22]([O:21][CH2:20][CH:18]2[C:19]3[CH:7]=[CH:8][CH:9]=[CH:10][C:11]=3[C:16]3[C:17]2=[CH:12][CH:13]=[CH:14][CH:15]=3)=[O:23])[C@@H:28]2[C@@H:31]([OH:34])[CH2:32][O:33][C@H:27]12

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 343679-Fluorenylmethyl chloroformateHCID 57551911HCID 57551911, compound

Product 1

HCID 46193050HCID 46193050, compoundYield 87%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 312751,4-DioxaneSolvent2×

Procedure

A solution of sodium carbonate (0.49 g, 4.63 mmol) in water (7.5 mL) followed by a solution of 9-fluorenylmethoxycarbonyl chloride (0.55 g, 2.13 mmol) in 1,4-dioxane (2.5 mL) was added dropwise over 15 minutes whilst stirring to a solution of aminoalcohol (69) in 1,4-dioxane (5 mL). The mixture was stirred for 60 minutes then water (50 mL) was added and the product extracted into dichloromethane (3×25 mL), then dried (Na2SO4), filtered and reduced in vacuo to leave a colourless oil. Flash chromatography over silica, eluting with ethyl acetate:heptane mixtures 10:90 to 45:55 gave alcohol (70) (623 mg, 87%) as a white solid. TLC (Rf=0.45, EtOAc:heptane 1:1), analytical HPLC single main peak, Rt=16.54 min., HPLC-MS 386.1/388.1 [M+H]+, 408.1/410.1 [M+Na]+; [α]D27.5−51.9° (c=2.31, CHCl3); (proton complex) δC (125 MHz, CDCl3) 47.21/47.41 (Fmoc CH), 53.30/53.43 (FmocNCH2), 57.74/58.36 (CHCl), 66.04/67.42 (Fmoc CH2), 67.87/68.52 (FmocNCH), 74.81/75.09 (OCH2CHOH), 74.92/75.51 (OCH 2CHOH), 86.57/87.24 (CHCHCl), 119.80/119.82/120.00/120.64/124.55/124.63/124.90/127.04/127.08/127.40/127.51/127.78/127.80/127.87 and 127.91 (aromatic CH), 141.21/141.29/141.38/143.44/143.70/143.88 and 143.91 (aromatic quaternary), 154.13/154.79 (Fmoc C═O).

Workup

  1. additionwas added dropwise over 15 minutes
  2. extractionthe product extracted into dichloromethane (3×25 mL)
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. customto leave a colourless oil
  6. washFlash chromatography over silica, eluting with ethyl acetate

Sources & evidence

ORD record
ord-7de2567abf2a4ebaac70126a8ec36af4
Source dataset
uspto-grants-2014_11
Patent number
US08877927B2

Reaction notes

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