Diisopropylethylamine → HCID 71060455, compound

HRID 1036693Notes

Reaction equation

HRID 1036693 reaction equation
[C:1]([O:5][C:6]([N:8]([CH3:22])[C:9]([CH3:21])([CH3:20])[C:10](ON1C(=O)CCC1=O)=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH2:23][C@H:24]([CH2:46][O:47][CH2:48][C:49]1[CH:54]=[CH:53][C:52]([CH3:55])=[CH:51][CH:50]=1)[C:25]([N:27]1[CH2:45][CH2:44][CH2:43][C:29]2([C:33](=[O:34])[N:32]([CH3:35])[CH2:31][CH:30]2[C:36]2[CH:41]=[CH:40][C:39]([F:42])=[CH:38][CH:37]=2)[CH2:28]1)=[O:26].CCN(C(C)C)C(C)C>C1COCC1.O>[F:42][C:39]1[CH:38]=[CH:37][C:36]([CH:30]2[C:29]3([CH2:43][CH2:44][CH2:45][N:27]([C:25](=[O:26])[C@H:24]([NH:23][C:10](=[O:11])[C:9]([N:8]([CH3:22])[C:6](=[O:7])[O:5][C:1]([CH3:3])([CH3:2])[CH3:4])([CH3:21])[CH3:20])[CH2:46][O:47][CH2:48][C:49]4[CH:54]=[CH:53][C:52]([CH3:55])=[CH:51][CH:50]=4)[CH2:28]3)[C:33](=[O:34])[N:32]([CH3:35])[CH2:31]2)=[CH:41][CH:40]=1

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 71060531HCID 71060531, compoundHCID 866740982,5-Dioxopyrrolidin-1-yl 2-(tert-butoxycarbonyl(methyl)amino)-2-methylpropanoate

Product 1

HCID 71060455HCID 71060455, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To 2,5-dioxopyrrolidin-1-yl 2-(tert-butoxycarbonyl(methyl)amino)-2-methylpropanoate (80 mg, 0.254 mmol) and 7-((R)-2-amino-3-(4-methylbenzyloxy)propanoyl)-4-(4-fluorophenyl)-2-methyl-2,7-diazaspiro[4.5]decan-1-one (115 mg, 0.254 mmol) in THF (3 ml) was added DIPEA (0.044 ml, 0.254 mmol) and the mixture stirred at RT overnight. The mixture was diluted with water (10 ml) and extracted with EtOAc (50 ml). The extracts were dried (MgSO4) and concentrated. The residue was applied to a 12 g silica cartridge which was eluted with ethyl acetate. The appropriate fractions were combined and concentrated to give tert-butyl 1-((2R)-1-(4-(4-fluorophenyl)-2-methyl-1-oxo-2,7-diazaspiro[4.5]decan-7-yl)-3-(4-methylbenzyloxy)-1-oxopropan-2-ylamino)-2-methyl-1-oxopropan-2-yl(methyl)carbamate as a foam.

Workup

  1. extractionextracted with EtOAc (50 ml)
  2. dry with materialThe extracts were dried (MgSO4)
  3. concentrationconcentrated
  4. washwas eluted with ethyl acetate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-b5cac5635fbd44439f33eb10fa7d5d59
Source dataset
uspto-grants-2013_10
Patent number
US08546416B2

Reaction notes

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