Diethylamine → tert-butyl N-{(2R,3R)-3-methoxy-2-methyl-3-[(2S)-pyrrolidin-2-yl]propanoyl}-L-phenylalaninate

HRID 74776Notes

Reaction equation

HRID 74776 reaction equation
C1C2C(COC([N:18]3[CH2:22][CH2:21][CH2:20][C@H:19]3[C@H:23]([O:44][CH3:45])[C@@H:24]([CH3:43])[C:25]([NH:27][C@H:28]([C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])[CH2:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)=[O:26])=O)C3C(=CC=CC=3)C=2C=CC=1.C(NCC)C>ClCCl>[CH3:45][O:44][C@@H:23]([C@@H:19]1[CH2:20][CH2:21][CH2:22][NH:18]1)[C@@H:24]([CH3:43])[C:25]([NH:27][C@H:28]([C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])[CH2:29][C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1)=[O:26]

Participants

4

Reactant 2

HCID 8021Diethylamine2×HCID 86762712tert-butyl N-[(2R,3R)-3-{(2S)-1[(9H-fluoren-9-ylmethoxy)carbonyl]pyrrolidin-2-yl}-3-methoxy-2-methylpropanoyl]-L-phenylalaninate

Product 1

HCID 86685746tert-butyl N-{(2R,3R)-3-methoxy-2-methyl-3-[(2S)-pyrrolidin-2-yl]propanoyl}-L-phenylalaninate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirring solution of #120 (2.87 g, 4.68 mmol, 1.00 eq.) in 20 mL of dichloromethane, diethylamine (10 mL, 95 mM, 20.5 eq.) was added. The reaction was allowed to stir at room temperature for 2 hours. Another (10 mL, 95 mmol, 20.5 eq.) of diethylamine was added and the reaction was allowed to stir at room temperature for 3 more hours. Reaction was concentrated in vacuo and placed underneath high vacuum producing #121 (1.8 g, quant.) yellow white oil solid mix. LC-MS (Protocol Q): m/z 391.1 [M+H+] retention time=1.05 minutes.

Workup

  1. stirringto stir at room temperature for 3 more hours
  2. customReaction
  3. concentrationwas concentrated in vacuo
  4. customproducing #121 (1.8 g, quant.) yellow white oil solid
  5. additionmix

Sources & evidence

ORD record
ord-73785a909cdd457ba35e45b10fccd219
Source dataset
uspto-grants-2014_09
Patent number
US08828401B2

Reaction notes

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