Trifluoroacetic acid → 2-Amino-2-methyl-N-((R)-1-((4S,5R)-2-methyl-1-oxo-4-phenyl-2,7-diazaspiro[4.5]decan-7-yl)-1-oxo-4-phenoxybutan-2-yl)propanamide

HRID 1036699Notes

Reaction equation

HRID 1036699 reaction equation
[CH3:1][C:2]([NH:37]C(=O)OC(C)(C)C)([CH3:36])[C:3]([NH:5][C@H:6]([CH2:27][CH2:28][O:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[C:7]([N:9]1[CH2:26][CH2:25][CH2:24][C@:11]2([C:15](=[O:16])[N:14]([CH3:17])[CH2:13][C@H:12]2[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:10]1)=[O:8])=[O:4].C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:37][C:2]([CH3:36])([CH3:1])[C:3]([NH:5][C@H:6]([CH2:27][CH2:28][O:29][C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1)[C:7]([N:9]1[CH2:26][CH2:25][CH2:24][C@:11]2([C:15](=[O:16])[N:14]([CH3:17])[CH2:13][C@H:12]2[C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH2:10]1)=[O:8])=[O:4]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 71060370tert-butyl 2-methyl-1-((R)-1-((4S,5R)-2-methyl-1-oxo-4-phenyl-2,7-diazaspiro[4.5]decan-7-yl)-1-oxo-4-phenoxybutan-2-ylamino)-1-oxopropan-2-ylcarbamate

Product 1

HCID 710604582-Amino-2-methyl-N-((R)-1-((4S,5R)-2-methyl-1-oxo-4-phenyl-2,7-diazaspiro[4.5]decan-7-yl)-1-oxo-4-phenoxybutan-2-yl)propanamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Tert-butyl 2-methyl-1-((R)-1-((4S,5R)-2-methyl-1-oxo-4-phenyl-2,7-diazaspiro[4.5]decan-7-yl)-1-oxo-4-phenoxybutan-2-ylamino)-1-oxopropan-2-ylcarbamate (38.7 mg; 0.064 mmol) was solubilised in DCM (0.5 ml). TFA (0.125 ml; 1.622 mmol) was added and the solution stirred at RT for 20 minutes before being concentrated in vacuo. The residual oil was dissolved in methanol (1 ml) and passed through a 1 g SCX-2 cartridge eluting with 2M NH3 in methanol (4 ml. Evaporation gave the title compound.

Workup

  1. concentrationbefore being concentrated in vacuo
  2. dissolutionThe residual oil was dissolved in methanol (1 ml)
  3. washeluting with 2M NH3 in methanol (4 ml
  4. customEvaporation

Sources & evidence

ORD record
ord-0daec5ce35ee46819805e094058b0a4f
Source dataset
uspto-grants-2013_10
Patent number
US08546416B2

Reaction notes

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