Acetic Acid → HCID 131711184, compound

HRID 2419481Notes

Reaction equation

HRID 2419481 reaction equation
[NH2:1][C@H:2]([C:12]([OH:14])=[O:13])[CH2:3][O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[CH3:15][CH2:16][N:17](CC)CC.[NH:22]([C:44]([O:46][C:47]([CH3:50])([CH3:49])[CH3:48])=[O:45])[C@H:23]([C:34](ON1C(=O)CCC1=O)=[O:35])[C@@H:24]([CH3:33])[O:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.[C:51]([OH:54])(=O)[CH3:52].CN(C=[O:59])C>>[NH:22]([C:44]([O:46][C:47]([CH3:48])([CH3:50])[CH3:49])=[O:45])[C@H:23]([C:34]([NH:1][C@H:2]([C:12]([O:14][N:17]1[C:51](=[O:54])[CH2:52][CH2:15][C:16]1=[O:59])=[O:13])[CH2:3][O:4][CH2:5][C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1)=[O:35])[C@@H:24]([CH3:33])[O:25][CH2:26][C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1

Participants

6

Reactant 5

HCID 176Acetic AcidHCID 6228DimethylformamideHCID 8471TriethylamineHCID 78457O-benzyl-L-serineHCID 12879029Boc-Thr(Bzl)-OSu

Product 1

HCID 131711184HCID 131711184, compound

Procedure

A suspension of H-Ser(Bzl)-OH (2.59 g, 13.28 mmol) in DMF (70 ml) was stirred with Et3N (2.0 ml) and Boc-Thr(Bzl)-OSu (6.0 g, 14.76 mmol) at 0° C for 2 hr and 25° C for 72 hr. The reaction mixture was acidified to about pH 3 with acetic acid and the solvents removed under reduced pressure. The resulting clear oil was extracted into ethyl acetate, washed with 5% AcOH and water, dried (MgSO4) and evaporated to a clear oil. The oil was dissolved in THF (100 ml) and treated with HOSu (1.8 g) and dicyclohexylcarbodiimide (DCC) (3.0 g) for 1.5 hr at 0° C and 25° C for 3 hr. The DCU was removed by filtration and the filtrate evaporated to a clear oil which was crystallized from ETOH, yield 5.3 g (70.4%); mp 112°-113° C; [α]D25 +18.7° (c 1, CHCl3).

Workup

  1. customthe solvents removed under reduced pressure
  2. extractionThe resulting clear oil was extracted into ethyl acetate
  3. washwashed with 5% AcOH and water
  4. dry with materialdried (MgSO4)
  5. customevaporated to a clear oil
  6. dissolutionThe oil was dissolved in THF (100 ml)
  7. additiontreated with HOSu (1.8 g) and dicyclohexylcarbodiimide (DCC) (3.0 g) for 1.5 hr at 0° C and 25° C for 3 hr
  8. customThe DCU was removed by filtration
  9. customthe filtrate evaporated to a clear oil which
  10. customwas crystallized from ETOH, yield 5.3 g (70.4%)

Sources & evidence

ORD record
ord-9b3e62575dcf4b4d9a7eabd999ff3fc1
Source dataset
uspto-grants-1978_08
Patent number
US04105652

Reaction notes

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