Di-tert-butyl glutamate hydrochloride → HCID 68695638, compound

HRID 629668Notes

Reaction equation

HRID 629668 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1[CH:17]=[CH:16][C:12]([C:13]([OH:15])=O)=[C:11]([N+:18]([O-:20])=[O:19])[CH:10]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C[N+:22](C)=C(N(C)C)ON1C2C=CC=CC=2N=N1.F[P-](F)(F)(F)(F)F.Cl.[C:46]([O:50][C:51](=[O:63])[C@H:52]([CH2:54][CH2:55][C:56]([O:58][C:59]([CH3:62])([CH3:61])[CH3:60])=[O:57])[NH2:53])([CH3:49])([CH3:48])[CH3:47]>ClCCl.C(N(CC)CC)C>[C:1]([O:5][C:6]([NH:8][C:9]1[CH:17]=[CH:16][C:12]([C:13]([NH:22][NH:53][C@H:52]([C:51]([O:50][C:46]([CH3:48])([CH3:49])[CH3:47])=[O:63])[CH2:54][CH2:55][C:56]([O:58][C:59]([CH3:62])([CH3:61])[CH3:60])=[O:57])=[O:15])=[C:11]([N+:18]([O-:20])=[O:19])[CH:10]=1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 3

HCID 208636Di-tert-butyl glutamate hydrochlorideHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 21951876HCID 21951876, compound

Product 1

HCID 68695638HCID 68695638, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8471TriethylamineSolvent

Procedure

To a mixture of 4-(tert-butoxycarbonylamino)-2-nitrobenzoic acid in 60 ml of dichloromethane were added 4.8 g of N,N,N′,N′-tetramethyl-O-(1H-benzotriazol-1-yl)-uronium-hexafluorophosphate. After stirring for 15 min. a mixture of 3.8 g of L-glutamic acid-di tert.-butylester hydrochloride in 60 ml dichloromethane and 3 ml triethylamine was added dropwise. After stirring for 20 hours at room temperature, the mixture was filtered and the filtrate was washed five times with 10% aqueous citric acid, four times with 5% aqueous sodium carbonate solution and two times with water. The organic layer was dried over magnesium sulphate and concentrated in vacuum to give 6.3 g of di-tert-butyl N-(4-(tert-butoxycarbonylamino)-2-nitrobenzamido)-L-glutamate as a yellow foam. This was directly used in example 3.

Workup

  1. additionwas added dropwise
  2. stirringAfter stirring for 20 hours at room temperature
  3. filtrationthe mixture was filtered
  4. washthe filtrate was washed five times with 10% aqueous citric acid, four times with 5% aqueous sodium carbonate solution and two times with water
  5. dry with materialThe organic layer was dried over magnesium sulphate
  6. concentrationconcentrated in vacuum

Sources & evidence

ORD record
ord-5050c73064234dc0801cc0c6f60729b4
Source dataset
uspto-grants-2016_04
Patent number
US09315506B2

Reaction notes

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