Methyl Acrylate → 3-[Benzyloxycarbonyl-((R)-2-tert-butoxycarbonylamino-1-methyl-ethyl)-amino]-propionic acid methyl ester

HRID 1096244Notes

Reaction equation

HRID 1096244 reaction equation
[C:1]([O:5][C:6](=[O:12])[NH:7][CH2:8][C@H:9]([NH2:11])[CH3:10])([CH3:4])([CH3:3])[CH3:2].[C:13]([O:17][CH3:18])(=[O:16])[CH:14]=[CH2:15].[CH2:19]([O:26][C:27](ON1C(=O)CCC1=O)=[O:28])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>CO>[CH3:18][O:17][C:13](=[O:16])[CH2:14][CH2:15][N:11]([C:27]([O:26][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:28])[C@H:9]([CH3:10])[CH2:8][NH:7][C:6]([O:5][C:1]([CH3:2])([CH3:4])[CH3:3])=[O:12]

Participants

5

Reactant 3

HCID 7294Methyl AcrylateHCID 83172Benzyl succinimido carbonateHCID 45072491tert-butyl N-((2R)-2-aminopropyl)carbamate

Product 1

HCID 667830553-[Benzyloxycarbonyl-((R)-2-tert-butoxycarbonylamino-1-methyl-ethyl)-amino]-propionic acid methyl esterYield 165.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

72 g (413 mmol) ((R)-2-amino-propyl)-carbamic acid tert-butyl ester were dissolved in MeOH (350 ml) in a jacketed reactor. A solution of 40 ml (438 mmol) methyl acrylate in MeOH (50 ml) was added over 10 min. After 15 h reaction at RT, 108 g (413 mmol) of N-benzyloxycarbonyloxy-succinimide were added in one portion. After 18 h, the reaction mixture was concentrated under reduced pressure affording a yellow oil (ca 270 g). The oil was re-dissolved in 300 mL MeOH and concentrated under reduced pressure (45° C./160-200 mbar) until constant weight to give 219 g of crude titled product as a yellow oil used directly in the next step.

Workup

  1. customAfter 15 h reaction at RT
  2. concentrationthe reaction mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-3ac629c8164c4f5fa64c436cb20f6919
Source dataset
uspto-grants-2012_03
Patent number
US08138175B2

Reaction notes

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