Diisopropylcarbodiimide → HCID 178454157, compound

HRID 1007967Notes

Reaction equation

HRID 1007967 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([C:17]([OH:19])=[O:18])[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N=C=NC(C)C)(C)C.[Si:29]([O:36][C:37]1[CH:42]=[C:41]([O:43][Si:44]([C:47]([CH3:50])([CH3:49])[CH3:48])([CH3:46])[CH3:45])[CH:40]=[CH:39][C:38]=1[C@H:51]1[CH2:56][CH2:55][C@H:54](O)[CH2:53][CH2:52]1)([C:32]([CH3:35])([CH3:34])[CH3:33])([CH3:31])[CH3:30]>ClCCl>[C:1]([O:5][C:6]([NH:8][C@H:9]([CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:17]([O:19][C@H:54]1[CH2:53][CH2:52][C@H:51]([C:38]2[CH:39]=[CH:40][C:41]([O:43][Si:44]([C:47]([CH3:49])([CH3:50])[CH3:48])([CH3:46])[CH3:45])=[CH:42][C:37]=2[O:36][Si:29]([C:32]([CH3:35])([CH3:34])[CH3:33])([CH3:30])[CH3:31])[CH2:56][CH2:55]1)=[O:18])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 12734DiisopropylcarbodiimideHCID 77857L-Phenylalanine, N-[(1,1-dimethylethoxy)carbonyl]-HCID 178455059HCID 178455059, compound

Product 1

HCID 178454157HCID 178454157, compoundYield 100.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a round bottomed flask was added N-(tert-butoxycarbonyl)-L-phenylalanine (109 mg) and dichloromethane (10 ml). To the solution was added diisopropylcarbodiimide (64 μl), trans-4-(2,4-bis{[tert-butyl(dimethyl)silyl]oxy}phenyl)cyclohexanol (150 mg) and 4-dimethyl aminopyridine (catalytic). The solution was stirred at room temperature for 15 hr. The reaction mixture was partitioned between water (20 ml) and dichloromethane (30 ml), the layers were separated and the aqueous phase was extracted with dichloromethane (2×30 ml). The combined organic phases were washed with brine (20 ml), dried over magnesium sulfate, filtered and concentrated in vacuo. Purification via flash chromatography (SiO2, ethyl acetate/petroleum ether, 1:19 v/v) furnished the title compound (236 mg, 100%) as a yellow oil. δH (CDCl3): 0.18 (6H, s), 0.23 (6H, s), 0.97 (9H, s), 1.03 (9H, s), 1.35-1.47 (13H, m), 1.80-1.90 (2H, m), 1.95-2.07 (2H, m), 2.77-2.86 (1H, m), 3.05-3.12 (2H, m), 4.49-4.58 (1H, m), 4.73-4.82 (1H, m), 4.93-5.00 (1H, m), 6.28 (1H, d), 6.40 (1H, dd), 6.93 (1H, d), 7.15 (2H, d), 7.19-7.31 (3H, m).

Workup

  1. customThe reaction mixture was partitioned between water (20 ml) and dichloromethane (30 ml)
  2. customthe layers were separated
  3. extractionthe aqueous phase was extracted with dichloromethane (2×30 ml)
  4. washThe combined organic phases were washed with brine (20 ml)
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customPurification via flash chromatography (SiO2, ethyl acetate/petroleum ether, 1:19 v/v)

Sources & evidence

ORD record
ord-439c9f7158f64b5db7e884b25052e0aa
Source dataset
uspto-grants-2004_09
Patent number
US06797731B2

Reaction notes

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