Hydrochloric Acid → Ammonium Hydroxide

HRID 1367256Notes

Reaction equation

HRID 1367256 reaction equation
Cl.Cl.[NH2:3][C@H:4]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH2:5][CH2:6][NH:7][C:8]1([C:13](OC)=[O:14])[CH2:12][CH2:11][CH2:10][CH2:9]1.Cl.C1C=NC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C>C1COCC1>[NH4+:3].[OH-:14].[C:17]1([C@H:4]2[NH:3][C:13](=[O:14])[C:8]3([CH2:12][CH2:11][CH2:10][CH2:9]3)[NH:7][CH2:6][CH2:5]2)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 181649HOAtHCID 66973378Methyl 1-{[(3S)-3-amino-3-phenylpropyl]amino}cyclopentanecarboxylate bis-hydrochloride2×

Product 2

HCID 14923Ammonium HydroxideHCID 66973323(9S)-9-phenyl-6,10-diazaspiro[4.6]undecan-11-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Potassium trimethylsilanoate (1.21 g, 9.45 mmol) was added to a stirred suspension of methyl 1-{[(3S)-3-amino-3-phenylpropyl]amino}cyclopentanecarboxylate bis-hydrochloride (1.00 g, 2.86 mmol, Intermediate 38) in THF (5.0 mL) at ambient temperature. After 4 h, the reaction mixture was adjusted to pH=8 with aqueous 1 M HCl. To this mixture was added HOAt (0.195 g, L43 mmol), and EDCI (0.549 g, 2.87 mmol). After 1 h, the reaction was concentrated in vacuo. The residue was partitioned between CH2Cl2 and water. The aqueous phase was extracted several times with CH2Cl2. The combined organic extracts were washed with saturated brine, then dried over MgSO4, filtered and concentrated in vacuo. The residue was purified by silica gel chromatography, eluting with CH2Cl2:MeOH:NH4OH—89.9:10:0.1 to give the title compound. MS: m/z=245 (M+1).

Workup

  1. waitAfter 1 h
  2. concentrationthe reaction was concentrated in vacuo
  3. customThe residue was partitioned between CH2Cl2 and water
  4. extractionThe aqueous phase was extracted several times with CH2Cl2
  5. washThe combined organic extracts were washed with saturated brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified by silica gel chromatography
  10. washeluting with CH2Cl2

Sources & evidence

ORD record
ord-e452a02631f84e318f7324d97ba86722
Source dataset
uspto-grants-2011_02
Patent number
US07893079B2

Reaction notes

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