Hydrochloric Acid → HCID 131716231, compound

HRID 329549Notes

Reaction equation

HRID 329549 reaction equation
Cl.[NH2:2][C@H:3]([C:8]([NH:10][CH2:11][C:12]([O:14][CH3:15])=[O:13])=[O:9])[CH2:4][CH:5]([CH3:7])[CH3:6].CCN(C(C)C)C(C)C.[CH3:25][C:26]([O:29][C:30]([NH:32][C@H:33]([C:43]([OH:45])=[O:44])[CH2:34][O:35][CH2:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)=[O:31])([CH3:28])[CH3:27].[NH2:46][CH2:47][C:48](O)=[O:49].C1C=CC(P(N=[N+]=[N-])(C2C=CC=CC=2)=O)=CC=1>CN(C=O)C.CCOC(C)=O.CCOCC.CCCCCC>[NH:32]([C:30]([O:29][C:26]([CH3:28])([CH3:27])[CH3:25])=[O:31])[C@H:33]([C:43]([OH:45])=[O:44])[CH2:34][OH:35].[NH:46]([CH2:36][C:37]1[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=1)[CH2:47][C:48]([NH:2][C@H:3]([C:8]([NH:10][CH2:11][C:12]([O:14][CH3:15])=[O:13])=[O:9])[CH2:4][CH:5]([CH3:6])[CH3:7])=[O:49]

Participants

10

Reactant 5

HCID 313Hydrochloric AcidHCID 81531DiisopropylethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 10943550HCID 10943550, compoundHCID 131716232HCID 131716232, compound

Product 2

HCID 98766N-[tert-butoxycarbonyl]-L-serineHCID 131716231HCID 131716231, compoundYield 146.3%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolventHCID 21584099Diethylether hexaneSolvent

Conditions

Temperature
0 °C

Procedure

Tetrapeptide H-Ser(Bzl)-Gly-Leu-Gly-OCH3 : HCl.H-Leu-Gly-OCH3 (12.2 g, 51.3 mmol) was dissolved in DMF (200 mL). DIEA (24 mL, 139.8 mmol) was added to the solution. This first solution was cooled to 0° C. A second solution of Boc-Ser-(Bzl)-Gly-OH (16.42 g, 46.6 mmol) and DPPA (14.1 g, 51.26 mmol) in DMF (122 mL) was added with stirring to the first solution. The mixture was stirred for 20 h while the temperature of the mixture gradually came to room temperature. Concentration of the reaction mixture under reduced pressure gave an oil. The oil was dissolved in EtOAc. The solution was washed with 1N HCl, 1N NaHCO3 and H2O, dried (Na2SO4 /MgSO4) and concentrated to dryness to give an oil. Trituration of the latter oil with Et2O-hexane yielded Boc-Ser(Bzl-Gly-Leu-Gly-OCH3 as a solid (23.82 g). The latter compound (28.82 g) was dissolved in 1N HCl in glacial acetic acid (100 mL). The mixture was stirred at room temperature for 1 h and then concentrated under reduced vacuum to give an oil. Trituration of the oil with Et2O afforded the tetrapeptide as a solid (19.71 g, HCl salt).

Workup

  1. stirringThe mixture was stirred for 20 h while the temperature of the mixture
  2. customgradually came to room temperature
  3. customConcentration of the reaction mixture under reduced pressure gave an oil
  4. washThe solution was washed with 1N HCl, 1N NaHCO3 and H2O
  5. dry with materialdried (Na2SO4 /MgSO4)
  6. concentrationconcentrated to dryness
  7. customto give an oil

Sources & evidence

ORD record
ord-29a1926728084fa1aaad95e46d3ea39c
Source dataset
uspto-grants-1990_01
Patent number
US04891358

Reaction notes

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