Methanol → Boc-Ser(Bzl)-Glu(OBzl)-OH

HRID 26330

Reaction equation

HRID 26330 reaction equation
[NH2:1][C@H:2]([C:15]([OH:17])=[O:16])[CH2:3][CH2:4][C:5](=[O:14])[O:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[NH:18]([C:39]([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40])[C@H:19]([C:29](ON1C(=O)CCC1=O)=[O:30])[CH2:20][O:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.CCN(CC)CC.CO>CN(C=O)C>[NH:18]([C:39]([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40])[C@H:19]([C:29]([NH:1][C@H:2]([C:15]([OH:17])=[O:16])[CH2:3][CH2:4][C:5](=[O:14])[O:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:30])[CH2:20][O:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 8471Triethylamine2×HCID 122337L-Glutamic acid, 5-(phenylmethyl) esterHCID 12879025Boc-Ser(Bzl)-OSu

Product 1

HCID 131711275Boc-Ser(Bzl)-Glu(OBzl)-OH

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

H-Glu(OBzl)-OH (39.4 g, 166 mmol) was stirred with Boc-Ser(Bzl)-OSu (65.0 g, 166 mmol) in 900 ml DMF overnight in the presence of Et3N (2.3 ml, 165 mmol). More Et3N was added during this time in order to maintain the reaction slightly basic. The clear solution was evaporated to dryness and the oily residue partitioned between EtOAc (1.5 liters) and 5% HOAc (2 liters). The organic layer was washed with H2O (2 times), dried over Na2SO4, and concentrated to a clear oil (90.0 g) which was taken up in 3 liters of ether and treated with 25 ml of cyclohexylamine The solid formed was recrystallized from MeOH and ether: yield, 76.2 (74.8%); mp 154°-156.5°; [α]D25 =+6.32° (c 1, MeOH).

Workup

  1. temperatureto maintain
  2. customthe reaction slightly basic
  3. customThe clear solution was evaporated to dryness
  4. customthe oily residue partitioned between EtOAc (1.5 liters) and 5% HOAc (2 liters)
  5. washThe organic layer was washed with H2O (2 times)
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated to a clear oil (90.0 g) which
  8. additiontreated with 25 ml of cyclohexylamine The solid
  9. customformed
  10. customwas recrystallized from MeOH and ether
  11. customyield

Sources & evidence

ORD record
ord-1ac4d583a5c84dbf8de08f1ac99a7c04
Source dataset
uspto-grants-1979_04
Patent number
US04148788

Linked notes

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