Diisopropylethylamine → HCID 70172690, compound
Reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([C:14]([OH:16])=O)[CH2:10][CH2:11][S:12][CH3:13])=[O:7])([CH3:4])([CH3:3])[CH3:2].C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.Cl.[NH2:51][C:52]1[C:61]2[C:56](=[CH:57][CH:58]=[C:59]([O:62][Si:63]([C:66]([CH3:69])([CH3:68])[CH3:67])([CH3:65])[CH3:64])[CH:60]=2)[C:55]([Br:70])=[CH:54][CH:53]=1.C(N(CC)C(C)C)(C)C>>[C:1]([O:5][C:6]([NH:8][C@H:9]([CH2:10][CH2:11][S:12][CH3:13])[C:14]([NH:51][C:52]1[C:61]2[C:56](=[CH:57][CH:58]=[C:59]([O:62][Si:63]([C:66]([CH3:68])([CH3:67])[CH3:69])([CH3:64])[CH3:65])[CH:60]=2)[C:55]([Br:70])=[CH:54][CH:53]=1)=[O:16])=[O:7])([CH3:2])([CH3:3])[CH3:4]Participants
5
Procedure
To (R)-N-(tert-butoxycarbonyl)methionine (1.33 g, 5.48 mmol) in dry H2Cl2 (5 mL) under argon were added PYBOP (2.85 g, 5.48 mmol), 1-amino-4-bromo-7-(tert-butyldimethylsilyloxy)naphthalene hydrochloride, as described above Step E, (800 mg, 2.19 mmol), and N,N-diisopropylethylamine (1.7 mL, 9.9 mmol). The reaction mixture was stirred for 3 hours, then partitioned between 10% aqueous citric acid (100 mL) and CH2Cl2 (100 mL). The organic extract was dried over Na2SO4, filtered, and concentrated in vacuo. The crude product was purified by flash column chromatography on silica, eluting with a gradient of hexane—5% EtOAc to hexane—20% EtOAc to yield the product as a pale foam.
Workup
- custompartitioned between 10% aqueous citric acid (100 mL) and CH2Cl2 (100 mL)
- extractionThe organic extract
- dry with materialwas dried over Na2SO4
- filtrationfiltered
- concentrationconcentrated in vacuo
- customThe crude product was purified by flash column chromatography on silica
- washeluting with a gradient of hexane—5% EtOAc to hexane—20% EtOAc
Sources & evidence
- ORD record
- ord-fc6b19aa69d2413da2cdeee8b2520a56
- Source dataset
- uspto-grants-2002_08
- Patent number
- US06441017B1
Reaction notes
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