Ammonia → HCID 22618325, compound

HRID 842132Notes

Reaction equation

HRID 842132 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:25]#[C:26][CH2:27][N:28]([C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])[O:29]C(OC(C)(C)C)=O)[C:5]2[O:9][C:8]([C:10]3[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[C:12]([O:18][CH:19]4[CH2:23][CH2:22][CH2:21][CH2:20]4)[CH:11]=3)=[N:7][C:6]=2[CH:24]=1.N>C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]([C:25]#[C:26][CH2:27][N:28]([C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])[OH:29])[C:5]2[O:9][C:8]([C:10]3[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[C:12]([O:18][CH:19]4[CH2:20][CH2:21][CH2:22][CH2:23]4)[CH:11]=3)=[N:7][C:6]=2[CH:24]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 22618314HCID 22618314, compound

Product 1

HCID 22618325HCID 22618325, compoundYield 57.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1.00 g (1.6 mmol) of 5-chloro-2-(3-cyclopentyloxy-4-methoxy-phenyl)-7-[3-(N-t-butyloxycarbonyl-N-t-butoxycarbonyloxy-amino)-1-propynyl]-benzoxazole was dissolved in 20 ml of THF and treated with 20 g of ammonia in a reactor. The pressure rose to 100 psi. After 2 hours, the solvents were removed in vacuo. Crystallization from methanol and recrystallization from di-isopropyl ether gave the title compound (0.47 g, 56.2%), mp 157-61° C.

Workup

  1. customthe solvents were removed in vacuo
  2. customCrystallization
  3. customfrom methanol and recrystallization from di-isopropyl ether

Sources & evidence

ORD record
ord-e3584b55b83b4346a45369e12066f739
Source dataset
uspto-grants-2002_04
Patent number
US06372770B1

Reaction notes

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