Ethylmorpholine → HCID 21344943, compound

HRID 2185661Notes

Reaction equation

HRID 2185661 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:20][CH3:21])[C:10]([N:12]1[CH2:19][CH2:18][CH2:17][C@H:13]1[C:14]([OH:16])=O)=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N1CCOCC1)C.ClC(OCC(C)C)=O.[CH2:38]([NH2:42])[CH2:39][CH2:40][CH3:41]>O1CCCC1.C(Cl)Cl>[CH2:38]([NH:42][C:14](=[O:16])[C@@H:13]1[CH2:17][CH2:18][CH2:19][N:12]1[C:10](=[O:11])[C@@H:9]([NH:8][C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[CH2:20][CH3:21])[CH2:39][CH2:40][CH3:41]

Participants

7

Reactant 4

HCID 7525EthylmorpholineHCID 8007ButylamineHCID 62365Isobutyl chloroformateHCID 11044788HCID 11044788, compound

Product 1

HCID 21344943HCID 21344943, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

2.42 g of 1-(N-(tert-butoxycarbonyl)-2(S)-aminobutyryl)-L-proline (8.05 mmol) prepared as in Example 2 c) are dissolved in dry tetrahydrofuran (15 ml). The solution is cooled in an ice/salt bath and 0.927 g of N-ethylmorpholine (8.05 mmol) and 1.10 g of isobutyl chloroformate (8.05 mmol) are then added. The solution is stirred for 45 minutes and 0.59 g (8.05 mmol) of n-butylamine is added. After stirring overnight, methylene chloride (200 ml) is added and the mixture is washed with 10% citric acid (2×100 ml) and then with 5% NaHCO3 (2×100 ml). The organic phase is dried (Na2SO4) and evaporated under vacuum. A syrup is obtained. The deprotection is carried out without characterization.

Workup

  1. temperatureThe solution is cooled in an ice/salt bath
  2. stirringAfter stirring overnight
  3. washthe mixture is washed with 10% citric acid (2×100 ml)
  4. dry with materialThe organic phase is dried (Na2SO4)
  5. customevaporated under vacuum
  6. customA syrup is obtained

Sources & evidence

ORD record
ord-8e3c4f0b6eea4456bf6597573880ca32
Source dataset
uspto-grants-2002_06
Patent number
US06403561B1

Reaction notes

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