Acetic Acid → HCID 131711189, compound

HRID 2419485Notes

Reaction equation

HRID 2419485 reaction equation
[NH2:1][C@H:2]([C:13]([OH:15])=[O:14])[C@@H:3]([CH3:12])[O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.CCN(CC)CC.[NH:23]([C:38]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39])[C@H:24]([C:28](ON1C(=O)CCC1=O)=[O:29])[CH:25]([CH3:27])[CH3:26].C(O)(=O)C>CN(C=O)C.C(Cl)(Cl)Cl>[NH:23]([C:38]([O:40][C:41]([CH3:43])([CH3:42])[CH3:44])=[O:39])[C@H:24]([C:28]([NH:1][C@H:2]([C:13]([OH:15])=[O:14])[C@@H:3]([CH3:12])[O:4][CH2:5][C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1)=[O:29])[CH:25]([CH3:26])[CH3:27]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 8471TriethylamineHCID 98768Boc-Val-osuHCID 6951054O-BENZYL-L-THREONINE

Product 1

HCID 131711189HCID 131711189, compound

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6228DimethylformamideSolvent

Procedure

A suspension of H-Thr(Bzl)-OH (3.0 g, 14.34 mmol) in DMF (60 ml) was mixed with Et3N (2 ml) and Boc-Val-OSu (4.96 g, 15.78 mmol) at 0° C for 2 hours and then at 25° C for 24 hours. Acetic acid was added to about pH 3 and the solvents removed under reduced pressure. The product was extracted into EtOAc, washed with 5% AcOH and water, dried (MgSO4) and evaporated to clear oil which crystallized from EtOAc with petroleum ether to yield 4.9 g (83.1%); mp 132°-135° C; [α]D25 +21.5° (c, 1, CHCl3). Anal. Calcd for C21H32N2O6 (408.49): C, 61.74; H, 7.89; N, 6.85. Found: C, 61.61; H, 7.76; N, 6.80.

Workup

  1. customthe solvents removed under reduced pressure
  2. extractionThe product was extracted into EtOAc
  3. washwashed with 5% AcOH and water
  4. dry with materialdried (MgSO4)
  5. customevaporated to clear oil which
  6. customcrystallized from EtOAc with petroleum ether
  7. customto yield 4.9 g (83.1%)

Sources & evidence

ORD record
ord-1d4909911b6249fabafaa203ad9671b7
Source dataset
uspto-grants-1978_08
Patent number
US04105652

Reaction notes

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