Hydrochloric Acid → HCID 67056933, compound

HRID 2201511Notes

Reaction equation

HRID 2201511 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][OH:8].C([O-])([O-])=O.[Na+].[Na+].[C:15](Cl)([O:17][CH2:18][CH:19]1[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[C:25]2[C:20]1=[CH:21][CH:22]=[CH:23][CH:24]=2)=[O:16].Cl>O.O1CCOCC1.CCOC(C)=O>[C:15]([CH:7]([OH:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][NH2:1])([O:17][CH2:18][CH:19]1[C:20]2[C:25](=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:26]2[C:31]1=[CH:30][CH:29]=[CH:28][CH:27]=2)=[O:16]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 199606-Amino-1-hexanolHCID 343679-Fluorenylmethyl chloroformate

Product 1

HCID 67056933HCID 67056933, compoundYield 97%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent2×

Procedure

6-Amino-hexan-1-ol (1.5 g, 12 mmol) was added to a vigorously stirred solution of Na2CO3 in H2O at 0° C. Dioxane (30 mL) was added, providing an opaque mixture. A solution of FmocCl, in dioxane (36 mL) was added dropwise at 0° C. The mixture was then allowed to warm to room temperature and was stirred for 1 hour. AcOEt (300 mL) was added, followed by HCl 0.1M (200 mL). The organic layer was washed with H2O (200 mL) and brine (50 mL), then dried over Na2SO4, filtered and concentrated. The crude product was purified by flash chromatography (CH2Cl2/MeOH, 97:3 to 90:10) to afford 3 as a white solid (3.95 g, 97%).

Workup

  1. customproviding an opaque mixture
  2. washThe organic layer was washed with H2O (200 mL) and brine (50 mL)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude product was purified by flash chromatography (CH2Cl2/MeOH, 97:3 to 90:10)

Sources & evidence

ORD record
ord-f030634796864747aae9af28f400dd2b
Source dataset
uspto-grants-2016_06
Patent number
US09364554B2

Reaction notes

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