2-(((Tert-butoxy)carbonyl)amino)-2-phenylacetic acid → HCID 60197432, compound

HRID 2370057Notes

Reaction equation

HRID 2370057 reaction equation
[C:1]([O:5][C:6]([NH:8][CH:9]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:10]([OH:12])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.O[C:44]1[CH:45]=[CH:46][C:47]([CH:50]=[C:51]2[NH:56][C:55](=[O:57])[C:54](=[CH:58][CH2:59][C:60]3[CH:65]=[CH:64][CH:63]=[CH:62]C=3)[NH:53][C:52]2=[O:66])=[N:48][CH:49]=1>CN(C=O)C>[C:1]([O:5][C:6]([NH:8][CH:9]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:10]([O:12][C:44]1[CH:49]=[N:48][C:47](/[CH:50]=[C:51]2\[NH:56][C:55](=[O:57])/[C:54](=[CH:58]/[C:59]3[CH:60]=[CH:65][CH:64]=[CH:63][CH:62]=3)/[NH:53][C:52]\2=[O:66])=[CH:46][CH:45]=1)=[O:11])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 5718052-(((Tert-butoxy)carbonyl)amino)-2-phenylacetic acidHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 69132345HCID 69132345, compound

Product 1

HCID 60197432HCID 60197432, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-(Tert-butoxycarbonylamino)-2-phenylacetic acid was dissolved in DMF and treated with HBTU. Compound C were then added into the mixture and stirred. After the completion of reaction, the reaction mixture was partitioned by K2CO3(aq) and CH2Cl2. The organic layer was collected, dried over MgSO4(s), and dried by rotary evaporator. The solid residues were then purified by column chromatography to get Compound 8. mp 198° C.; 1H-NMR (400 MHz, CDCl3): δ 1.50 (s, 9H), 5.48 (s, 1H), 5.58-5.59 (m, 1H), 6.78 (s, 1H), 7.11 (s, 1H), 7.37-7.50 (m, 13H), 8.22 (s, 1H), 8.42 (s, 1H), 12.46 (s, 1H).

Workup

  1. customAfter the completion of reaction
  2. customthe reaction mixture was partitioned by K2CO3(aq) and CH2Cl2
  3. customThe organic layer was collected
  4. dry with materialdried over MgSO4(s)
  5. customdried by rotary evaporator
  6. customThe solid residues were then purified by column chromatography

Sources & evidence

ORD record
ord-3601a140706143b9b770ebbca0bd4bcd
Source dataset
uspto-grants-2014_04
Patent number
US08710062B2

Reaction notes

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