Triethylamine → HCID 70090354, compound

HRID 326535Notes

Reaction equation

HRID 326535 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:16]([OH:18])=O)[CH:13]([CH3:15])[CH3:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:19]([O:23][C:24](=[O:32])[CH2:25][NH:26][CH:27]1[CH2:31][CH2:30][CH2:29][CH2:28]1)([CH3:22])([CH3:21])[CH3:20].C(N(CC)CC)C.O=C1N(P(Cl)(N2CCOC2=O)=O)CCO1>ClCCl>[C:19]([O:23][C:24](=[O:32])[CH2:25][N:26]([C:16](=[O:18])[C@H:12]([CH:13]([CH3:14])[CH3:15])[NH:11][C:9]([O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)=[O:10])[CH:27]1[CH2:28][CH2:29][CH2:30][CH2:31]1)([CH3:22])([CH3:20])[CH3:21]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 152842Bis(2-oxo-3-oxazolidinyl)phosphinic chlorideHCID 726987N-Carbobenzoxy-L-valineHCID 13298943Tert-butyl 2-(cyclopentylamino)acetate

Product 1

HCID 70090354HCID 70090354, compoundYield 85.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of N-benzyloxycarbonyl-L-valine (50.0 g) and N-cyclopentylglycine t-butyl ester (39.8 g) in dichloromethane (1.3 liter), stirred under nitrogen and cooled in an ice bath to 0°-5° C., was added triethylamine (44.5 g) then bis(2-oxo-3-oxazolidinyl)phosphinic chloride (56.0 g) at 0° C. The stirred mixture was allowed to warm to room temperature overnight before it was evaporated. After the residue was partitioned between water (1 liter) and ethyl acetate (1 liter), the ethyl acetate solution was washed (1N hydrochloric acid (twice), water, saturated sodium bicarbonate, brine), dried (MgSO4) and evaporated. The residue was purified by flash chromatography, eluting with ethyl acetate:dichloromethane (0:100, 5:95, 10:90 and 25:75, successively). A first, mixed fraction was rechromatographed and the product obtained combined with the product obtained from the first chromatography to afford the ester (73.4 g, 85%); TLC, Rf =0.30, ethyl acetate:dichloromethane (5:95); MS, m/e=433 (M+1), 377, 325, 269, 234, 286, 162, 144 91(base).

Workup

  1. temperaturecooled in an ice bath to 0°-5° C.
  2. customat 0° C
  3. customwas evaporated
  4. customAfter the residue was partitioned between water (1 liter) and ethyl acetate (1 liter)
  5. washthe ethyl acetate solution was washed (1N hydrochloric acid (twice), water, saturated sodium bicarbonate, brine),
  6. dry with materialdried (MgSO4)
  7. customevaporated
  8. customThe residue was purified by flash chromatography
  9. washeluting with ethyl acetate:dichloromethane (0:100, 5:95, 10:90 and 25:75
  10. additionA first, mixed fraction
  11. customwas rechromatographed
  12. customthe product obtained
  13. customobtained from the first chromatography

Sources & evidence

ORD record
ord-ce0b5972848841bab8251100e48418f9
Source dataset
uspto-grants-1993_12
Patent number
US05270301

Reaction notes

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