Thiomorpholine → HCID 52530575, compound

HRID 651132Notes

Reaction equation

HRID 651132 reaction equation
[NH:1]1[CH2:6][CH2:5][S:4][CH2:3][CH2:2]1.[C:7]([NH:14][C@H:15]([C:23](O)=[O:24])[CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8]>>[C:10]([O:9][C:7](=[O:8])[NH:14][C@@H:15]([CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:23](=[O:24])[N:1]1[CH2:6][CH2:5][S:4][CH2:3][CH2:2]1)([CH3:13])([CH3:11])[CH3:12]

Participants

3

Reactant 2

HCID 67164ThiomorpholineHCID 77857L-Phenylalanine, N-[(1,1-dimethylethoxy)carbonyl]-

Product 1

HCID 52530575HCID 52530575, compound

Procedure

Thiomorpholine (38 mmol) and Boc-L-phenylalanine (19 mmol) were coupled according to Procedure A (0-25° C. reaction temperature) with the following work up: the reaction mixture was concentrated, diluted with ethyl acetate, then washed first with 1 N HCl three times, then with 2 N NaOH, the organic layer dried over MgSO4 and concentrated. The resulting foam was used without further purification. Yield 6.3 g, 95%.

Workup

  1. concentrationthe reaction mixture was concentrated
  2. additiondiluted with ethyl acetate
  3. washwashed first with 1 N HCl three times
  4. dry with materialwith 2 N NaOH, the organic layer dried over MgSO4
  5. concentrationconcentrated
  6. customThe resulting foam was used without further purification

Sources & evidence

ORD record
ord-fada9252b5d044288097f48f7f3820b5
Source dataset
uspto-grants-2001_08
Patent number
US06277877B1

Reaction notes

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