Triethylamine → (S)-methyl 2-(tert-butoxycarbonylamino)-3-(4-(isopropylcarbamoyloxy)phenyl)propanoate

HRID 449472

Reaction equation

HRID 449472 reaction equation
[N:1]([CH:4]([CH3:6])[CH3:5])=[C:2]=[O:3].[C:7]([O:11][C:12]([NH:14][C@@H:15]([CH2:20][C:21]1[CH:26]=[CH:25][C:24]([OH:27])=[CH:23][CH:22]=1)[C:16]([O:18][CH3:19])=[O:17])=[O:13])([CH3:10])([CH3:9])[CH3:8].C(N(CC)CC)C>C(Cl)Cl>[C:7]([O:11][C:12]([NH:14][C@@H:15]([CH2:20][C:21]1[CH:26]=[CH:25][C:24]([O:27][C:2](=[O:3])[NH:1][CH:4]([CH3:6])[CH3:5])=[CH:23][CH:22]=1)[C:16]([O:18][CH3:19])=[O:17])=[O:13])([CH3:10])([CH3:8])[CH3:9]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 61277Isopropyl isocyanateHCID 7019130Boc-Tyr-OMe

Product 1

HCID 59496584(S)-methyl 2-(tert-butoxycarbonylamino)-3-(4-(isopropylcarbamoyloxy)phenyl)propanoateYield 80%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-Isocyanatopropane (Aldrich, Cat. #141070) (22 mg, 0.25 mmol) was added to a solution of methyl (2S)-2-[(tert-butoxycarbonyl)amino]-3-(4-hydroxyphenyl)propanoate (50 mg, 0.2 mmol) and triethylamine (26 mg, 0.25 mmol) in methylene chloride (2 mL). The reaction was stirred for 1 h. The reaction was partitioned between water and ethyl acetate. The organic phase was washed with saturated brine, dried over magnesium sulfate, filtered and concentrated under reduced pressure to give crude product, (S)-methyl 2-(tert-butoxycarbonylamino)-3-(4-(isopropylcarbamoyloxy)phenyl)propanoate (50 mg, 80%) as a white solid. Analytical LCMS (M+H-Boc)+: m/z=281.0.

Workup

  1. customThe reaction was partitioned between water and ethyl acetate
  2. washThe organic phase was washed with saturated brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-e79e9a3b3f1a4e6a875c3838f7851f09
Source dataset
uspto-grants-2013_07
Patent number
US08481732B2

Linked notes

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