Butylamine → HCID 57544612, compound

HRID 2355340Notes

Reaction equation

HRID 2355340 reaction equation
CCN=C=NCCCN(C)C.Cl.[C:13]([O:17][C:18]([NH:20][C@@H:21]([CH2:25][CH:26]1[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]1)[C:22]([OH:24])=O)=[O:19])([CH3:16])([CH3:15])[CH3:14].C(N(C(C)C)CC)(C)C.C1[CH:42]=[CH:43][C:44]2N(O)N=[N:47][C:45]=2C=1.C(N)CCC>CN(C1C=CN=CC=1)C.CN(C=O)C>[CH2:45]([NH:47][C:22](=[O:24])[C@@H:21]([NH:20][C:18](=[O:19])[O:17][C:13]([CH3:14])([CH3:15])[CH3:16])[CH2:25][CH:26]1[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]1)[CH2:44][CH2:43][CH3:42]

Participants

8

Reactant 5

HCID 8007ButylamineHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 10588189(2S)-2-(((tert-butoxy)carbonyl)amino)-3-cyclohexylpropanoic acid

Product 1

HCID 57544612HCID 57544612, compoundYield 127.7%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

Solid EDC.HCl (518 mg, 3.3 mmol) was added to a solution of (S)-2-(tert-butoxycarbonylamino)-3-cyclohexylpropanoic acid (405 mg, 1.5 mmol), diisopropylethylamine (2.5 mL, 14 mmol), HOBt (130 mg, 1.0 mmol), DMAP (18 mg, 0.15 mmol), butylamine (0.30 mL, 3 mmol), and anhydrous DMF (25 mL). The resulting clear light yellow solution was stirred at rt for 12 h. The solvent was removed (50° C., 150 Torr) and the residue was taken up in ether (100 mL) and washed with satd aq NaHCO3 (3×10 mL). Hexanes (30 mL) was added to the ether extract and this was washed with water (5×5 mL) and brine (3×5 mL), dried (Na2SO4), decanted, stripped and the crude material was purified using 40 g SiO2 with an eluent of hexanes to 30% MeOH in EA. Combining appropriate fractions and removal of solvent gave (S)-tert-butyl 1-(butylamino)-3-cyclohexyl-1-oxopropan-2-ylcarbamate (417 mg, 85%) as a white solid. 1H NMR (CDCl3) δ 0.80-1.80 (m 20H), 1.50 (s, 9H), 3.20 (m, 2H), 4.01 (d, 1H), 5.01 (d, 1H), 6.50 (bs, 1H). MS ESI+ve m/z 321 (M+Na).

Workup

  1. customThe solvent was removed (50° C., 150 Torr)
  2. washwashed with satd aq NaHCO3 (3×10 mL)
  3. additionHexanes (30 mL) was added to the ether
  4. extractionextract
  5. washthis was washed with water (5×5 mL) and brine (3×5 mL)
  6. dry with materialdried (Na2SO4)
  7. customdecanted
  8. customthe crude material was purified
  9. customfractions and removal of solvent

Sources & evidence

ORD record
ord-50636f6f5bc4487d8b900a4dfe1a5f70
Source dataset
uspto-grants-2010_07
Patent number
US07754737B2

Reaction notes

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