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Water → (R)-2-(2-(tert-Butoxycarbonylamino)-2-methylpropanamido)-4-phenylbutanoic acid

HRID 1036737
Notes
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Reaction equation

HRID 1036737 reaction equation
O=C1CCC(=O)N1[C:8](=[O:20])[C:9]([NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:11])[CH3:10].[CH:21]1[CH:26]=[CH:25][C:24]([CH2:27][CH2:28][C@@H:29]([NH2:33])[C:30]([OH:32])=[O:31])=[CH:23][CH:22]=1.O.C(N(CC)CC)C>C1COCC1>[C:15]([O:14][C:13]([NH:12][C:9]([CH3:11])([CH3:10])[C:8]([NH:33][C@H:29]([CH2:28][CH2:27][C:24]1[CH:23]=[CH:22][CH:21]=[CH:26][CH:25]=1)[C:30]([OH:32])=[O:31])=[O:20])=[O:19])([CH3:18])([CH3:17])[CH3:16]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 6950302D-HomophenylalanineHCID 71060486Tert-butyl 1-(2,5-dioxopyrrolidin-1-yl)-2-methyl-1-oxopropan-2-ylcarbamate

Product 1

HCID 22862434(R)-2-(2-(tert-Butoxycarbonylamino)-2-methylpropanamido)-4-phenylbutanoic acid

Reagents, catalysts & solvents 1

HCID 8028
Tetrahydrofuran
Solvent

Conditions

Temperature
50 °C

Procedure

A mixture comprising of tert-Butyl 1-(2,5-dioxopyrrolidin-1-yl)-2-methyl-1-oxopropan-2-ylcarbamate (1 g, 3.52 mmol) (prepared according to the procedure described in EP1486498A1 page 20) and H-D-Homophe-OH (0.630 g, 3.52 mmol) in THF (16 ml)/water (4 ml) was treated with triethylamine (1.471 ml, 10.55 mmol). The reaction mixture was stirred at 50° C. for 9 hours. THF was removed in vacuo. The aqueous solution was further diluted with water and the pH adjusted to pH 2-3 using 1M HCl. The resulting aqueous phase was extracted with EtOAc. The organic portion was dried (MgSO4) and concentrated in vacuo to afford the title compound.

Workup

  1. customTHF was removed in vacuo
  2. additionThe aqueous solution was further diluted with water
  3. extractionThe resulting aqueous phase was extracted with EtOAc
  4. dry with materialThe organic portion was dried (MgSO4)
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-dc4a3cf71c9c482baed69d543722a3d6
Source dataset
uspto-grants-2013_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08546416B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes