Diisopropylethylamine → HCID 70149057, compound

HRID 2187883Notes

Reaction equation

HRID 2187883 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([C:11]([OH:13])=O)[CH3:10])=[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.[NH2:48][C:49]1[C:58]2[C:53](=[CH:54][CH:55]=[C:56]([O:59][Si:60]([C:73]([CH3:76])([CH3:75])[CH3:74])([C:67]3[CH:72]=[CH:71][CH:70]=[CH:69][CH:68]=3)[C:61]3[CH:66]=[CH:65][CH:64]=[CH:63][CH:62]=3)[CH:57]=2)[CH:52]=[CH:51][CH:50]=1.C(N(CC)C(C)C)(C)C>C(Cl)Cl>[C:1]([O:5][C:6]([NH:8][C@H:9]([CH3:10])[C:11]([NH:48][C:49]1[C:58]2[C:53](=[CH:54][CH:55]=[C:56]([O:59][Si:60]([C:73]([CH3:76])([CH3:75])[CH3:74])([C:61]3[CH:62]=[CH:63][CH:64]=[CH:65][CH:66]=3)[C:67]3[CH:72]=[CH:71][CH:70]=[CH:69][CH:68]=3)[CH:57]=2)[CH:52]=[CH:51][CH:50]=1)=[O:13])=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 637606BOC-D-alanineHCID 2724699PyBOPHCID 18475842HCID 18475842, compound

Product 1

HCID 70149057HCID 70149057, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To (R)-N-(tert-butoxycarbonyl)alanine (220 mg, 1.16 mmol) in dry CH2Cl2 (2 mL) under argon were added PYBOP (604 mg, 1.16 mmol), 1-amino-7-(tert-butyldiphenylsilyloxy)naphthalene hydrochloride, as described above in Step C, (250 mg, 0.58 mmol), and N,N-diisopropylethylamine (0.40 mL, 2.3 mmol). The reaction mixture was stirred for 3 hrs, then partitioned between CH2Cl2 (250 mL) and 10% aqueous citric acid (75 mL). The organic layer was dried over Na2SO4, filtered, and concentrated in vacuo. The residue was purified by flash column chromatography on silica, eluting with CH2Cl2-20% ethyl acetate to yield the desired product as a white foam.

Workup

  1. custompartitioned between CH2Cl2 (250 mL) and 10% aqueous citric acid (75 mL)
  2. dry with materialThe organic layer was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by flash column chromatography on silica
  6. washeluting with CH2Cl2-20% ethyl acetate

Sources & evidence

ORD record
ord-6b4a0e53e7a04dca8cf9af7017f1729b
Source dataset
uspto-grants-2002_06
Patent number
US06410534B1

Reaction notes

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