Ammonia → HCID 59581287, compound

HRID 386611Notes

Reaction equation

HRID 386611 reaction equation
[CH3:1][N:2]1[C@@:6]2([CH2:14][C:13]3[C:8](=[CH:9][CH:10]=[C:11]([NH:15][C:16](=[O:26])[CH2:17][NH:18]C(=O)OC(C)(C)C)[CH:12]=3)[CH2:7]2)[C:5](=[O:27])[NH:4][C:3]1=[O:28].Cl.N>CCOC(C)=O.CO>[NH2:18][CH2:17][C:16]([NH:15][C:11]1[CH:12]=[C:13]2[C:8](=[CH:9][CH:10]=1)[CH2:7][C@@:6]1([C:5](=[O:27])[NH:4][C:3](=[O:28])[N:2]1[CH3:1])[CH2:14]2)=[O:26]

Participants

6

Reactant 3

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 59581301HCID 59581301, compound

Product 1

HCID 59581287HCID 59581287, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of tert-butyl (2-{[(4S)-3-methyl-2,5-dioxo-1′,3′-dihydrospiro[imidazolidine-4,2′-inden]-5′-yl]amino}-2-oxoethyl)carbamate from Step A (1.80 g, 4.63 mmol) in EtOAc (50 mL), at 0° C., was added anhydrous HCl (bubbled in through a pipet, for 5 minutes). After an additional 30 minutes of standing at 0° C., the solvent and excess HCl was removed in vacuo to yield a solid. This solid was then dissolved in the minimal amount of MeOH and treated with a methanolic 2 N ammonia solution (20 mL, 40 mmol). This mixture was stirred for 30 min at ambient temperature, before the bulk of the MeOH was removed in vacuo. The residue was applied to a silica gel column for purification, eluting with DCM:MeOH (10% conc. NH4OH)—95:5 to 85:15. Product containing fractions were pooled and concentrated in vacuo to give the title compound. MS: m/z=289 (M+1).

Workup

  1. custombubbled in through a pipet, for 5 minutes)
  2. customthe solvent and excess HCl was removed in vacuo
  3. customto yield a solid
  4. customwas removed in vacuo
  5. customThe residue was applied to a silica gel column for purification
  6. washeluting with DCM
  7. additionProduct containing fractions
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4ddc311037eb443f9aaffd8e22c2f2d9
Source dataset
uspto-grants-2013_02
Patent number
US08372859B2

Reaction notes

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