Triethylamine → HCID 73294501, compound

HRID 530528Notes

Reaction equation

HRID 530528 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C@@H:16]([OH:18])[CH3:17])[C:13]([OH:15])=O)=[O:10])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7].CCN(CC)CC.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F>C(Cl)Cl>[CH2:1]([O:8][C:9](=[O:10])[NH:11][C@H:12]1[C:13](=[O:15])[O:18][C@H:16]1[CH3:17])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 86699952HCID 86699952, compound

Product 1

HCID 73294501HCID 73294501, compoundYield 37%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Under nitrogen atmosphere at 0° C., to a stirred mixture of employing (2R,3S)-2-(heptoxycarbonylamino)-3-hydroxy-butanoic acid (0.3 g, 1.14 mmol) in dry CH2Cl2 (30 mL), Et3N (0.48 mL, 3.44 mmol) and subsequently TBTU (0.44 g, 1.37 mmol) were added. The mixture was left stirring 1 h at 0° C. and 15 h at rt. Upon full conversion of the starting material, the organics were removed under reduced pressure, and the resulting crude product absorbed over silica gel and purified by typical column chromatography, eluting with Cy:EtOAc (from 100:0 to 0:100) to afford the title compound (0.10 g, 37%), as white solid.

Workup

  1. additionwere added
  2. waitThe mixture was left
  3. customUpon full conversion of the starting material, the organics were removed under reduced pressure
  4. customthe resulting crude product absorbed over silica gel
  5. custompurified by typical column chromatography
  6. washeluting with Cy

Sources & evidence

ORD record
ord-f90f8f6b4fde40b388339c767f7dcc43
Source dataset
uspto-grants-2016_05
Patent number
US09353075B2

Reaction notes

Loading…