Diisopropylethylamine → Methyl 1-({(3S)-3-[(tert-butoxycarbonyl)amino]-3-phenylpropyl}amino)cyclopentanecarboxylate

HRID 1866696Notes

Reaction equation

HRID 1866696 reaction equation
O=[CH:2][CH2:3][C@H:4]([NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.Cl.[NH2:20][C:21]1([C:26]([O:28][CH3:29])=[O:27])[CH2:25][CH2:24][CH2:23][CH2:22]1.CCN(C(C)C)C(C)C.C([O-])(O)=O.[Na+]>C(Cl)(Cl)Cl.O>[C:14]([O:13][C:12]([NH:11][C@H:4]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)[CH2:3][CH2:2][NH:20][C:21]1([C:26]([O:28][CH3:29])=[O:27])[CH2:25][CH2:24][CH2:23][CH2:22]1)=[O:18])([CH3:17])([CH3:16])[CH3:15]

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 516892Sodium Bicarbonate2×HCID 11513856Methyl 1-amino-1-cyclopentanecarboxylate, HClHCID 11817535Boc-(S)-3-Amino-3-phenylpropanal

Product 1

HCID 66973463Methyl 1-({(3S)-3-[(tert-butoxycarbonyl)amino]-3-phenylpropyl}amino)cyclopentanecarboxylate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent

Procedure

To a solution of tert-butyl [(1S)-3-oxo-1-phenylpropyl]carbamate from Step B (0.820 g, 3.29 mmol) and methyl 1-aminocyclopentanecarboxylate hydrochloride (0.591 g, 3.29 mmol) in chloroform (33 mL) was added Hunig's base (0.574 mL, 3.29 mmol). After stirring at ambient temperature for 20 min, NaHB(OAc)3 (1.74 g, 8.22 mmol) was added as a solid. Upon completion of the reaction, saturated aqueous NaHCO3 (3 mL) was added and the mixture was allowed to stir for at least 2 h. Water (5 mL) and additional saturated NaHCO3 (3 mL) was then added to form two layers. The aqueous layer was extracted once with chloroform (50 mL). The combined organic layers were dried over sodium sulfate, filtered and concentrated in vacuo to give an oil. This oil was purified by silica gel chromatography, eluting with a gradient of MeOH:DCM 1:99 to 6:94, to give the title compound. MS: m/z=377 (M+1).

Workup

  1. additionwas added
  2. stirringto stir for at least 2 h
  3. customto form two layers
  4. extractionThe aqueous layer was extracted once with chloroform (50 mL)
  5. dry with materialThe combined organic layers were dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customto give an oil
  9. customThis oil was purified by silica gel chromatography
  10. washeluting with a gradient of MeOH:DCM 1:99 to 6:94

Sources & evidence

ORD record
ord-d4f1496dcce74edebcfdfa3fedcd27ef
Source dataset
uspto-grants-2009_12
Patent number
US07629338B2

Reaction notes

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