Hydrochloric Acid → HCID 131726070, compound

HRID 722984Notes

Reaction equation

HRID 722984 reaction equation
Cl.[NH2:2][C@H:3]([C:20]([O:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=[O:21])[CH2:4][CH2:5][CH2:6][CH2:7][NH:8][C:9]([O:11][CH2:12][C:13]1[CH:19]=[CH:18][CH:17]=[CH:16][C:14]=1[Cl:15])=[O:10].[NH:30]([C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])[C@H:31]([C:33](O)=[O:34])[CH3:32].ON1C2C=CC=CC=2N=N1.C1(N=C=NC2CCCCC2)CCCCC1>O1CCCC1.C(Cl)(Cl)Cl.CO>[NH:30]([C:36]([O:38][C:39]([CH3:40])([CH3:42])[CH3:41])=[O:37])[C@H:31]([C:33]([NH:2][C@H:3]([C:20]([O:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=[O:21])[CH2:4][CH2:5][CH2:6][CH2:7][NH:8][C:9]([O:11][CH2:12][C:13]1[CH:19]=[CH:18][CH:17]=[CH:16][C:14]=1[Cl:15])=[O:10])=[O:34])[CH3:32]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 85082Tert-butoxycarbonylalanine2×HCID 7408677HCID 7408677, compound

Product 1

HCID 131726070HCID 131726070, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 21584188Chloroform methanolSolvent

Conditions

Temperature
0 °C

Procedure

At 0° C. the solution of 88 mg (0.2 mmol) of HCl.Lys(ClZ)-OBzl in 5 ml of anhydrous tetrahydrofuran was adjusted to pH 9, to which the pre-cold solution of 38 mg (0.2 mmol) of Boc-Ala-OH, 30 mg (0.22 mmol) of 1-hydroxybenzotriazole and 45 mg (0.22 mmol) of dicyclohexylcarbodiimide in 5 ml of anhydrous tetrahydrofuran was added. The reaction mixture was stirred at 0° C. for 2 h and at room temperature for 5 h and TLC (chloroform/methanol, 30:1) indicated complete disappearance of Boc-Ala-OH. The resulted precipitates of N,N-dicyclohexylurea were filtrated and the filtrate was diluted with 20 ml of ethyl acetate. The solution obtained was washed successively with saturated NaCO3 in water (30 ml×3), saturated NaCl in water (30 ml×3) and KHSO4 in water (5%, 30 ml×3). The separated ethyl acetate layer was dried with anhydrous MgSO4, and then evaporated to provide 112 mg (98%) of the title compound as a colorless powder. Mp94–96° C., FAB-MS (m/e) 575[M+H]+, 475[M-Boc]+.

Workup

  1. customAt 0° C.
  2. additionwas added
  3. customThe resulted precipitates of N,N-dicyclohexylurea
  4. filtrationwere filtrated
  5. additionthe filtrate was diluted with 20 ml of ethyl acetate
  6. customThe solution obtained
  7. washwas washed successively with saturated NaCO3 in water (30 ml×3), saturated NaCl in water (30 ml×3)
  8. dry with materialThe separated ethyl acetate layer was dried with anhydrous MgSO4
  9. customevaporated

Sources & evidence

ORD record
ord-5b2f0dd5d8264366a39fe8689cace323
Source dataset
uspto-grants-2006_11
Patent number
US07138491B2

Reaction notes

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