Acetic Acid → (s)-{[4-(Tert-butoxycarbonylamino-methyl)-cyclohexylmethyl]-amino}-phenyl-acetic acid cyclopentyl ester

HRID 548271Notes

Reaction equation

HRID 548271 reaction equation
[C:1]([O:5][C:6](=[O:17])[NH:7][CH2:8][CH:9]1[CH2:14][CH2:13][CH:12]([CH:15]=O)[CH2:11][CH2:10]1)([CH3:4])([CH3:3])[CH3:2].[CH:18]1([O:23][C:24](=[O:33])[C@@H:25]([NH2:32])[C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH2:22][CH2:21][CH2:20][CH2:19]1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C([O-])(O)=O.[Na+]>ClCCCl.C(Cl)Cl>[CH:18]1([O:23][C:24](=[O:33])[C@@H:25]([NH:32][CH2:15][CH:12]2[CH2:13][CH2:14][CH:9]([CH2:8][NH:7][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:17])[CH2:10][CH2:11]2)[C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH2:22][CH2:21][CH2:20][CH2:19]1

Participants

8

Reactant 5

HCID 176Acetic AcidHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 15408001trans-4-[(Boc-amino)methyl]cyclohexanecarbaldehydeHCID 57658397(S)-Amino-phenyl-acetic acid cyclopentyl ester

Product 1

HCID 57971740(s)-{[4-(Tert-butoxycarbonylamino-methyl)-cyclohexylmethyl]-amino}-phenyl-acetic acid cyclopentyl esterYield 31.3%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 6344DichloromethaneSolvent

Procedure

(4-Formyl-cyclohexylmethyl)-carbamic acid tert-butyl ester (390 mg, 1.6 mmol) and (S)-amino-phenyl-acetic acid cyclopentyl ester (394 mg, 1.8 mmol) were stirred in DCE (6 ml) at r.t. for 25 min. Acetic acid (9.6 μl, 0.16 mmol) and sodium triacetoxy-borohydride (1.0 g, 4.8 mmol) were added and the resulting mixture was stirred for 1 h30 at r.t. DCM (10 ml) and a saturated solution of NaHCO3 (10 ml) were added and phases were separated. Aqueous were extracted with EtOAc (2×10 ml), the organics were dried over magnesium sulfate, filtered and evaporated to dryness. The crude product was purified by column chromatography (8:2 heptane/EtOAc) to yield 223 mg of the pure amine (31% yield). LCMS purity 100%, m/z 445 [M++H]+.

Workup

  1. customphases were separated
  2. extractionAqueous were extracted with EtOAc (2×10 ml)
  3. dry with materialthe organics were dried over magnesium sulfate
  4. filtrationfiltered
  5. customevaporated to dryness
  6. customThe crude product was purified by column chromatography (8:2 heptane/EtOAc)

Sources & evidence

ORD record
ord-ff80201ee0a24ce48da703ec72166d1f
Source dataset
uspto-grants-2011_05
Patent number
US07939666B2

Reaction notes

Loading…