Reaction equation
C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.[CH3:34][O:35][P:36]([CH:39]([NH:43][C:44]([O:46][CH2:47][C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1)=[O:45])[CH:40]([CH3:42])[CH3:41])(=O)[OH:37].[CH3:54][O:55][C:56](=[O:70])[CH:57]([OH:69])[CH2:58][CH2:59][CH2:60][NH:61][C:62]([O:64][C:65]([CH3:68])([CH3:67])[CH3:66])=[O:63].CCN(C(C)C)C(C)C>CN(C=O)C.C(OCC)(=O)C>[CH3:54][O:55][C:56](=[O:70])[CH:57]([O:69][P:36]([CH:39]([NH:43][C:44]([O:46][CH2:47][C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1)=[O:45])[CH:40]([CH3:42])[CH3:41])([O:35][CH3:34])=[O:37])[CH2:58][CH2:59][CH2:60][NH:61][C:62]([O:64][C:65]([CH3:67])([CH3:66])[CH3:68])=[O:63]Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
A solution of PyBOP (2.1 g, 4.0 mmol) in DMF (3 mL) was added to a mixture of (1-benzyloxycarbonylamino-2-methyl-propyl)-phosphonic acid monomethyl ester (1.0 g, 3.32 mmol) and 5-tert-butoxycarbonylamino-2-hydroxy-pentanoic acid methyl ester (865 mg, 3.5 mmol) in DMF (4 mL) under argon. DIPEA (2.28 mL, 13.3 mmol) was added dropwise and the mixture was stirred over night. Ethyl acetate was added and the mixture was washed with 10% KHSO4, satd. NaHCO3 and brine and dried. Concentration under reduced pressure followed by chromathography (heptane/EtOAc, 1:1→1:6) gave 2-[(1-benzyloxycarbonylamino-2-methyl-propyl)-methoxy-phosphinoyloxy]-5-tert-butoxycarbonylamino-pentanoic acid methyl ester (1.21 g, 69%).
Workup
- washthe mixture was washed with 10% KHSO4
- dry with materialNaHCO3 and brine and dried
- concentrationConcentration under reduced pressure
Sources & evidence
- ORD record
- ord-8a578daed5af45c78522723ae5936fd0
- Source dataset
- uspto-grants-2008_04
- Patent number
- US07354895B1
Linked notes
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