6-carboxy-N2-[[[carboxy-2-[(1-oxoheptyl)amino]ethyl]amino]carbonyl]-N6-[(1,1-dimethylethoxy)carbonyl]-L-lysyl-D-alanine → N-[6-carboxy-N2-[[[2-carboxy-2-[(1-oxoheptyl)amino]-ethyl]amino]carbonyl]-L-lysyl]-D-alanine

HRID 52258Notes

Reaction equation

HRID 52258 reaction equation
[C:1]([CH:4]([NH:35]C(OC(C)(C)C)=O)[CH2:5][CH2:6][CH2:7][C@@H:8]([C:27]([NH:29][C@@H:30]([C:32]([OH:34])=[O:33])[CH3:31])=[O:28])[NH:9][C:10]([NH:12][CH2:13][CH:14]([C:24]([OH:26])=[O:25])[NH:15][C:16](=[O:23])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])=[O:11])([OH:3])=[O:2]>C(O)(C(F)(F)F)=O>[C:1]([CH:4]([NH2:35])[CH2:5][CH2:6][CH2:7][C@@H:8]([C:27]([NH:29][C@@H:30]([C:32]([OH:34])=[O:33])[CH3:31])=[O:28])[NH:9][C:10]([NH:12][CH2:13][CH:14]([C:24]([OH:26])=[O:25])[NH:15][C:16](=[O:23])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])=[O:11])([OH:3])=[O:2]

Participants

3

Reactant 1

HCID 867497186-carboxy-N2-[[[carboxy-2-[(1-oxoheptyl)amino]ethyl]amino]carbonyl]-N6-[(1,1-dimethylethoxy)carbonyl]-L-lysyl-D-alanine

Product 1

HCID 54072783N-[6-carboxy-N2-[[[2-carboxy-2-[(1-oxoheptyl)amino]-ethyl]amino]carbonyl]-L-lysyl]-D-alanine

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

To 85.9 mg of 1b-5 under argon is treated with 500 μl of TFA according to Example 80. The volatiles are evaporated to a residue which is triturated with ether 3x and the ether is decanted. The residue is dried to give 77.9 mg of 1b-11 as a white solid. NMR(CD3OD) δ0.80(t,3H), 2.16(t,2H), 3.22 (br s, 5H), 3.58 (m, 2H), 3.85 (m, 1H), 4.15 (m, 1H), 4.30(d, 1H), 4.40(m,1H); MS(HR-FAB) m/z 526.2482 (M+H, calcd for C21H38N5O9 526.2489).

Workup

  1. customThe volatiles are evaporated to a residue which
  2. customis triturated with ether 3x
  3. customthe ether is decanted
  4. customThe residue is dried
  5. customto give 77.9 mg of 1b-11 as a white solid

Sources & evidence

ORD record
ord-0a5c804113b94030bb3c425b75f1123e
Source dataset
uspto-grants-1997_04
Patent number
US05616612

Reaction notes

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