Triethylamine → HCID 86700011, compound

HRID 530568Notes

Reaction equation

HRID 530568 reaction equation
[CH3:1][C:2]([CH3:26])([O:13][C:14]([NH:16][C@H:17]([C@H:21]([OH:25])[CH:22]([CH3:24])[CH3:23])[C:18](O)=[O:19])=[O:15])[CH2:3][CH2:4][CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.CC(C)(OC(N[C@H]([C@@H](O)C(C)C)C(O)=O)=O)CCCCC1C=CC=CC=1.CCN(CC)CC.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F>C(Cl)Cl>[CH3:1][C:2]([O:13][C:14](=[O:15])[NH:16][C@H:17]1[C:18](=[O:19])[O:25][C@@H:21]1[CH:22]([CH3:24])[CH3:23])([CH3:26])[CH2:3][CH2:4][CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 86700012HCID 86700012, compoundHCID 86700013HCID 86700013, compound

Product 1

HCID 86700011HCID 86700011, compoundYield 18%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Under nitrogen atmosphere, to a stirred mixture of (2R*,3R*)-2-[(1,1-dimethyl-5-phenyl-pentoxy)-carbonylamino]-3-hydroxy-4-methyl-pentanoic acid and (2R*,3S*)-2-[(1,1-dimethyl-5-phenyl-pentoxy)-carbonylamino]-3-hydroxy-4-methyl-pentanoic acid (0.11 g, 0.30 mmol) in dry CH2Cl2 (15 mL), at 0° C., Et3N (0.126 mL, 0.9 mmol) and subsequently TBTU (0.116 g, 0.36 mmol) were added. The mixture was left stirring at 0° C. for 1 h and at rt for 15 h. The organics were then removed under reduced pressure, and the resulting crude product purified by column chromatography, using a Teledyne ISCO apparatus, eluting with Cy:AcOEt (from 100:0 to 80:20) to afford the pure title compound (0.019 g, 18%), as pure anti diastereoisomer, as white solid. MS (ESI) m/z: 365 [M−NH4]+; (ESI) m/z: 346 [M−H]−. 1H NMR (DMSO-d6) δ 0.86 (d, J=6.66 Hz, 3H), 0.95 (d, J=6.54 Hz, 3H), 1.27-1.35 (m, 2H), 1.36 (s, 6H), 1.55 (p, J=7.56 Hz, 2H), 1.66-1.85 (m, 2H), 1.96 (dt, J=6.52, 8.91 Hz, 1H), 2.57 (t, J=7.71 Hz, 2H), 4.17 (dd, J=4.40, 9.09 Hz, 1H), 4.69 (dd, J=4.40, 8.33 Hz, 1H), 7.11-7.33 (m, 5H), 7.81 (d, J=8.32 Hz, 1H).

Workup

  1. waitThe mixture was left
  2. customThe organics were then removed under reduced pressure
  3. customthe resulting crude product purified by column chromatography
  4. washeluting with Cy

Sources & evidence

ORD record
ord-1c046653f4524096a62b198e68f86317
Source dataset
uspto-grants-2016_05
Patent number
US09353075B2

Reaction notes

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