Ethylamine → HCID 89346575, compound

HRID 1773095Notes

Reaction equation

HRID 1773095 reaction equation
[CH3:1][C:2]([O:5][C:6]([NH:8][C@H:9]([C:22]([OH:24])=O)[CH2:10][CH2:11][C:12]([O:14]CC1C=CC=CC=1)=[O:13])=[O:7])([CH3:4])[CH3:3].Cl.C[N:27](C)[CH2:28][CH2:29]CN=C=NCC.O.ON1C2C=CC=CC=2N=N1.C(N)C>CN(C=O)C.[OH-].[Na+].C(N(CC)CC)C>[C:2]([O:5][C:6]([NH:8][C@H:9]([C:22](=[O:24])[NH:27][CH2:28][CH3:29])[CH2:10][CH2:11][C:12]([OH:14])=[O:13])=[O:7])([CH3:1])([CH3:3])[CH3:4]

Participants

8

Reactant 4

HCID 6341EthylamineHCID 83589L-Glutamic acid, N-((1,1-dimethylethoxy)carbonyl)-, 5-(phenylmethyl) esterHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrate

Product 1

HCID 89346575HCID 89346575, compound

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolventHCID 14798Sodium HydroxideSolvent

Procedure

337 mg (1.0 mmol) of Boc-Glu (OBzl)-OH, 191 mg (1.0 mmol) of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride, 152 mg (1.0 mmol) of 1-hydroxybenzotriazole monohydrate and 0.5 ml of triethylamine were suspended in 4.0 ml of DMF, to which 150 μl of 33% aqueous ethylamine solution was added. Following agitation at room temperature overnight, extraction was performed with ethyl acetate/water. The organic layer was washed with saturated saline and added with sodium sulfate for drying. The organic layer was subjected to vacuum condensation. The resulting residue was dissolved in 4.0 ml of 10% aqueous sodium hydroxide solution and stirred overnight. Purification step A was used to obtain a crude product of the title compound.

Workup

  1. additionwas added
  2. customat room temperature
  3. extractionovernight, extraction
  4. washThe organic layer was washed with saturated saline
  5. additionadded with sodium sulfate
  6. customfor drying
  7. customThe organic layer was subjected to vacuum condensation
  8. customPurification step A

Sources & evidence

ORD record
ord-fc7b628b8fc44dbb8704a8128aca4da8
Source dataset
uspto-grants-2016_02
Patent number
US09253997B2

Reaction notes

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