Water → HCID 9818008, compound

HRID 1057297Notes

Reaction equation

HRID 1057297 reaction equation
[C:1]([C:5]1[CH:28]=[CH:27][C:8]([O:9][CH:10]2[CH2:13][N:12]([CH:14](C3C=CC=CC=3)C3C=CC=CC=3)[CH2:11]2)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].C(Cl)(Cl)=[O:30].O.[NH2:34][CH2:35][C@H:36]([OH:38])[CH3:37]>ClCCl>[C:1]([C:5]1[CH:6]=[CH:7][C:8]([O:9][CH:10]2[CH2:11][N:12]([C:14]([NH:34][CH2:35][C@H:36]([OH:38])[CH3:37])=[O:30])[CH2:13]2)=[CH:27][CH:28]=1)([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 4

HCID 962WaterHCID 6371PhosgeneHCID 439938(2R)-1-aminopropan-2-olHCID 18671362HCID 18671362, compound

Product 1

HCID 9818008HCID 9818008, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of compound (1) (2.30 g, 6.19 mmol) in dichloromethane (25 mL) was treated with phosgene solution (ca. 20 wt. % in toluene; 3.28 mL, 6.2 mmol) with water cooling. The solution was stirred for 1 h, cooled to 0° C., and (R)-1-amino-2-propanol (1.08 mL, 1.03 g, 13.7 mmol) added dropwise. The solution was stirred for 18 h. Dichloromethane (25 mL) was added, and the solution was washed with 1-M HCl (25 mL), dried (Na2SO4), and concentrated in vacuo. The crude product was purified by chromatography [SiO2; MeOH-ethyl acetate-hexane (0:2:3→0:1:0→1:9:0)] and triturated with ether to give the title compound (1.15 g, 61%) as a white solid, m.p. 98-99° C. Found: C, 66.5; H, 8.8; N, 9.1. C17H26N2O3 requires C, 66.6; H, 8.55; N, 9.1%.

Workup

  1. stirringThe solution was stirred for 18 h
  2. washthe solution was washed with 1-M HCl (25 mL)
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated in vacuo
  5. customThe crude product was purified by chromatography [SiO2; MeOH-ethyl acetate-hexane (0:2:3→0:1:0→1:9:0)]
  6. customtriturated with ether

Sources & evidence

ORD record
ord-9023312523d04dd6adaf09e9a7defd31
Source dataset
uspto-grants-2003_02
Patent number
US06514961B1

Reaction notes

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