Diisopropylethylamine → HCID 86659551, compound

HRID 455907Notes

Reaction equation

HRID 455907 reaction equation
[C:1]([NH:8]CCN)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[CH:12]([N:15](C(C)C)CC)(C)[CH3:13].[Br:21][C:22]([CH3:27])([CH3:26])[C:23](Br)=[O:24].C(OCC)(=O)C.ClCCl>ClCCl>[C:1]([NH:8][C:23](=[O:24])[C:22]([Br:21])([CH3:27])[CH2:26][CH2:13][CH2:12][NH2:15])([O:3][C:4]([CH3:5])([CH3:7])[CH3:6])=[O:2]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 886852-Bromo-2-methylpropionyl bromideHCID 187201N-BOC-ethylenediamineHCID 21226138Dichloromethane ethylacetate

Product 1

HCID 86659551HCID 86659551, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of N-Boc-ethylenediamine (5.0 mL, 32 mmol), and diisopropylethylamine (5.8 mL, 33 mmol) in anhydrous dichloromethane (35 mL) was cooled in a NaCl/ice bath (−10° C., bath temperature). Over a period of 15 minutes, 2-bromoisobutyryl bromide (4.1 mL, 33 mmol) was added to this solution. After 1 h, the ice bath was removed and the reaction was allowed to warm to room temperature and stirring was continued for 18 h. The reaction mixture was concentrated to dryness under reduced pressure giving a tan colored solid which was dry-loaded onto a silica gel column. The product was isolated by elution with ethyl acetate:dichloromethane (3:2) as an off-white solid (7.84 g, 80%). 1H NMR (CDCl3, 300 MHz): δ 7.2 (bs, 1H), 4.91 (bs, 1H), 3.33 (m, 4H), 1.93 (s, 6H), 1.43 (s, 9H). 13C NMR (CDCl3, 300 MHz): δ 172.9, 157.1, 80.1, 61.9, 42.0, 40.0, 32.5, 28.6. EIMS m/z: 331 ([M+Na]+), 333 ([M+Na]+).

Workup

  1. waitAfter 1 h
  2. customthe ice bath was removed
  3. waitwas continued for 18 h
  4. concentrationThe reaction mixture was concentrated to dryness under reduced pressure
  5. customgiving a tan colored solid which

Sources & evidence

ORD record
ord-8dc1ef4ebcf24e6eaccef729824af1cc
Source dataset
uspto-grants-2013_07
Patent number
US08497356B2

Reaction notes

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