Ethyl Acetate → HCID 131734634, compound
Reaction equation
[NH2:1][C@H:2]([C:7]([O:9][CH2:10][CH2:11][N:12]([CH2:15][CH3:16])[CH2:13][CH3:14])=[O:8])[CH2:3][CH2:4][S:5][CH3:6].[F:17][C:18]([C:21]([OH:23])=[O:22])([F:20])[F:19].[NH:24](C(OC(C)(C)C)=O)[CH2:25][C:26]([NH:28][C@H:29]([C:37](ON1C(=O)CCC1=O)=[O:38])[CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)=[O:27].C(OCC)(=O)C>C([O-])(O)=O.[Na+].CC(C)=O>[NH2:24][CH2:25][C:26]([NH:28][C@H:29]([C:37]([NH:1][C@H:2]([C:7]([O:9][CH2:10][CH2:11][N:12]([CH2:13][CH3:14])[CH2:15][CH3:16])=[O:8])[CH2:3][CH2:4][S:5][CH3:6])=[O:38])[CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)=[O:27].[F:17][C:18]([C:21]([OH:23])=[O:22])([F:20])[F:19]Participants
6
Procedure
25 g of H-Met-OCH2CH2N(CH2CH3)2.TFA was dissolved in 300 ml of 5% NaHCO3. 22 g of Boc-Gly-Phe-OSu in 150 ml of acetone was added into the reaction mixture. The mixture was stirred for 5 h at RT. 500 ml of ethyl acetate was added into the mixture. The ethyl acetate solution was washed with water (3×100 ml). The organic solution was dried over sodium sulfate. The solution was evaporated to dryness. The residue was dissolved in 250 ml of dichloromethylene. 200 ml of trifluoroacetic acid was added into the mixture and the mixture was stirred for 30 min. The mixture was evaporated to dryness to yield 25 g of H-Gly-Phe-Met-OCH2CH2N(CH2CH3)2.TFA.
Workup
- washThe ethyl acetate solution was washed with water (3×100 ml)
- dry with materialThe organic solution was dried over sodium sulfate
- customThe solution was evaporated to dryness
- dissolutionThe residue was dissolved in 250 ml of dichloromethylene
- addition200 ml of trifluoroacetic acid was added into the mixture
- stirringthe mixture was stirred for 30 min
- customThe mixture was evaporated to dryness
Sources & evidence
- ORD record
- ord-651de0eed71141a4b75eb92761145b38
- Source dataset
- uspto-grants-2016_02
- Patent number
- US09248109B2
Reaction notes
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