Butylamine → HCID 14158041, compound

HRID 1535087Notes

Reaction equation

HRID 1535087 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[C@@H:15]([CH2:16][CH:17]2[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]2)[C@H:14]([CH2:23][CH:24]([CH:28]([CH3:30])[CH3:29])[C:25](O)=[O:26])[O:13][C:12]1([CH3:32])[CH3:31])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:33]([NH2:37])[CH2:34][CH2:35][CH3:36].C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C>CN(C=O)C.C(N(CC)CC)C>[CH2:1]([O:8][C:9]([N:11]1[C@@H:15]([CH2:16][CH:17]2[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22]2)[C@H:14]([CH2:23][C@@H:24]([CH:28]([CH3:29])[CH3:30])[C:25]([NH:37][CH2:33][CH2:34][CH2:35][CH3:36])=[O:26])[O:13][C:12]1([CH3:32])[CH3:31])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 8007ButylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 14158038HCID 14158038, compound

Product 1

HCID 14158041HCID 14158041, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

The crude carboxylic acid (I) (551 mg) was dissolved in DMF (10 ml) containing triethylamine (126 mg). Butylamine (109 mg), HOBT (169 mg) and EDAC (240 mg) were added and the solution was allowed to stand overnight. The solvent was removed by evaporation and the residue partitioned between ethyl acetate (20 ml) and water (20 ml). The organic layer was separated and washed with saturated sodium hydrogen carbonate solution (20 ml), followed by water (20 ml) and then saturated sodium chloride solution (20 ml). The organic phase was dried (MgSO4) and the solvent was removed by evaporation. The residue was purified by flash chromatography eluting with ethyl acetate/hexane (1:4 v/v), to give initially (2S)-2-[(4S,5S)-3-benzyloxycarbonyl-4-cyclohexylmethyl-2,2-dimethyl-1,3-oxazolidin-5-yl]methyl-N-butyl-3-methylbutanamide (J), as a clear oil (103 mg); NMR (CDCl3): 0.9 (m, 9H), 1.0-2.1 (complex m, 27H), 3.25 (q, 2H), 3.75 (m, 2H), 5.1 (dd, 2H), 5.6 (br, 1H), 7.3 (m, 5H); and then the corresponding (2R)-isomer, as a clear oil (133 mg); NMR (CDCl3): 0.9 (m, 9H), 1.0-2.1 (complex m, 27H), 3.25 (m, 2H), 3.75 (m, 1H), 3.9 (m, 1H), 5.1 (dd, 2H), 5.4 (br, 1H), 7.4 (m, 5H).

Workup

  1. customThe solvent was removed by evaporation
  2. customthe residue partitioned between ethyl acetate (20 ml) and water (20 ml)
  3. customThe organic layer was separated
  4. washwashed with saturated sodium hydrogen carbonate solution (20 ml)
  5. dry with materialThe organic phase was dried (MgSO4)
  6. customthe solvent was removed by evaporation
  7. customThe residue was purified by flash chromatography
  8. washeluting with ethyl acetate/hexane (1:4 v/v)

Sources & evidence

ORD record
ord-0b336d5326a245c48ea8ccab980b1e17
Source dataset
uspto-grants-1992_02
Patent number
US05091425

Reaction notes

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