Water → Di-tert-butyl {2-[(3-{[1-methyl-5-(tritylamino)pyrazol-4-yl]amino}-3-oxopropanoyl)amino]-1,3-propanediyl}biscarbamate

HRID 459616Notes

Reaction equation

HRID 459616 reaction equation
[CH3:1][N:2]1[C:6]([NH:7][C:8]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[C:5]([NH:27][C:28](=[O:33])[CH2:29][C:30](O)=[O:31])[CH:4]=[N:3]1.[NH2:34][CH:35]([CH2:45][NH:46][C:47](=[O:53])[O:48][C:49]([CH3:52])([CH3:51])[CH3:50])[CH2:36][NH:37][C:38](=[O:44])[O:39][C:40]([CH3:43])([CH3:42])[CH3:41].Cl.CN(C)CCCN=C=NCC.O>O1CCCC1.C(Cl)Cl>[CH3:1][N:2]1[C:6]([NH:7][C:8]([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[C:5]([NH:27][C:28](=[O:33])[CH2:29][C:30]([NH:34][CH:35]([CH2:45][NH:46][C:47](=[O:53])[O:48][C:49]([CH3:52])([CH3:51])[CH3:50])[CH2:36][NH:37][C:38](=[O:44])[O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:31])[CH:4]=[N:3]1

Participants

7

Reactant 4

HCID 962WaterHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 15186003tert-butyl N-(2-amino-3-{[(tert-butoxy)carbonyl]amino}propyl)carbamateHCID 219045813-{[1-Methyl-5-(tritylamino)pyrazol-4-yl]amino}-3-oxopropanoic acid

Product 1

HCID 86760458Di-tert-butyl {2-[(3-{[1-methyl-5-(tritylamino)pyrazol-4-yl]amino}-3-oxopropanoyl)amino]-1,3-propanediyl}biscarbamateYield 72.1%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 3-{[1-methyl-5-(tritylamino)pyrazol-4-yl]amino}-3-oxopropanoic acid (600 mg), di-tert-butyl (2-amino-1,3-propanediyl)biscarbamate (434 mg) and N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (522 mg) in tetrahydrofuran (12 ml) and methylene chloride (6 ml) was stirred overnight at room temperature. Water was added and the whole mixture was extracted with ethyl acetate. The organic layer was washed with water and brine, and dried over anhydrous magnesium sulfate. Concentration under reduced pressure gave a residue, which was triturated with diisopropyl ether-ethyl acetate (2:1) to give di-tert-butyl {2-[(3-{[1-methyl-5-(tritylamino)pyrazol-4-yl]amino}-3-oxopropanoyl)amino]-1,3-propanediyl}biscarbamate (699 mg) as a white solid.

Workup

  1. extractionthe whole mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with water and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationConcentration under reduced pressure
  5. customgave a residue, which
  6. customwas triturated with diisopropyl ether-ethyl acetate (2:1)

Sources & evidence

ORD record
ord-38bc5a0323cd4b3cbe293dd33a169905
Source dataset
uspto-grants-2007_03
Patent number
US07192943B2

Reaction notes

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