N-(tert-butoxycarbonyl)glycine → HCID 76281969, compound

HRID 539586Notes

Reaction equation

HRID 539586 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[N:10][N:11]3[CH:16]=[CH:15][C:14]([C:17]([N:19]([C:21]4[CH:26]=[CH:25][C:24]([C:27]#[N:28])=[CH:23][CH:22]=4)[CH3:20])=[O:18])=[CH:13][C:12]=23)=[CH:4][CH:3]=1.C(OC([NH:36][CH2:37][C:38](O)=[O:39])=O)(C)(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>C(Cl)Cl>[NH2:36][CH2:37][C:38]([NH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[N:10][N:11]3[CH:16]=[CH:15][C:14]([C:17]([N:19]([C:21]4[CH:22]=[CH:23][C:24]([C:27]#[N:28])=[CH:25][CH:26]=4)[CH3:20])=[O:18])=[CH:13][C:12]=23)=[CH:4][CH:3]=1)=[O:39]

Participants

5

Reactant 3

HCID 78288N-(tert-butoxycarbonyl)glycineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 76281968HCID 76281968, compound

Product 1

HCID 76281969HCID 76281969, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of Example 42 (1.0 equiv.) in CH2Cl2 (˜0.1 M) was treated with 2-((tert-butoxycarbonyl)amino)acetic acid (1.2 equiv.), followed by HATU (1.1 equiv(2.5 equiv.). The resulting mixture was allowed to stir at rt for two hours, and then was filtered and treated with one volume of TFA. The resulting solution was allowed to stir at rt for 30 minutes, and the solvents were removed under reduced pressure. The residue was purified by mass-triggered HPLC to provide the desired product. ESI-MS (m/z): [M+H]+ 425.1, RT 1.1033 min.

Workup

  1. filtrationwas filtered
  2. additiontreated with one volume of TFA
  3. stirringto stir at rt for 30 minutes
  4. customthe solvents were removed under reduced pressure
  5. customThe residue was purified by mass-triggered HPLC

Sources & evidence

ORD record
ord-87024e59382b4c5d8dc453f85ca10b68
Source dataset
uspto-grants-2014_10
Patent number
US08871754B2

Reaction notes

Loading…