L-Pyroglutamic Acid → HCID 67018543, compound

HRID 490051Notes

Reaction equation

HRID 490051 reaction equation
[CH:1]([O:4][C:5](=[O:39])[O:6][CH:7]1[CH:11]2[O:12][Si](C(C)(C)C)(C(C)(C)C)[O:14][CH2:15][CH:10]2[O:9][CH:8]1[N:24]1[C:28]2[N:29]=[C:30]([N:33]=[CH:34][N:35]([CH3:37])[CH3:36])[N:31]=[CH:32][C:27]=2[S:26][C:25]1=[O:38])([CH3:3])[CH3:2].N1C(=O)CC[C@H]1C(O)=O>CO>[CH:1]([O:4][C:5](=[O:39])[O:6][CH:7]1[CH:11]([OH:12])[CH:10]([CH2:15][OH:14])[O:9][CH:8]1[N:24]1[C:28]2[N:29]=[C:30]([N:33]=[CH:34][N:35]([CH3:37])[CH3:36])[N:31]=[CH:32][C:27]=2[S:26][C:25]1=[O:38])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 7405L-Pyroglutamic AcidHCID 67018565HCID 67018565, compound

Product 1

HCID 67018543HCID 67018543, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Carbonic acid 2,2-di-tert-butyl-6-[5-(dimethylamino-methyleneamino)-2-oxo-thiazolo[4,5-d]pyrimidin-3-yl]-tetrahydro-furo[3,2-d][1,3,2]dioxasilin-7-yl ester isopropyl ester (1.70 g, 2.92 mmol) (14) was dissolved in anhydrous MeOH (10.0 mL) and HF/Pyr (245 uL) was added. The clear colorless reaction suddenly thickened with a white precipitate within 5 min. The reaction was stirred 15 min then conc in vacuo. The solids were triturated with EtOAc then dried at 40° C. 16 h to obtain 1.22 g (95%) of 15 as a flocculent snow white solid: 1H NMR (400 MHz, DMSO-d6) δ 8.72 (1H, s), 8.64 (1H, s), 6.11 (1H, d, J=9.1 Hz), 5.84 (1H, d, J=4.1 Hz), 5.57 (1H, dd, J1=1.2 Hz, J2=3.9 Hz), 4.66-4.74 (2H, m), 4.24-4.28 (2H, m), 4.24-4.28 (1H, m), 3.97-4.01 (1H, m), 3.56-3.73 (2H, m), 3.14 (3H, s), 3.04 (3H, s), 1.18 (3H, dd, J1=0.0 Hz, J2=0.0 Hz), 1.20 (3H, d, J=6.2 Hz), 1.17 (3H, d, J=6.2 Hz); [M+H]+ @ m/z 442.5.

Workup

  1. customThe clear colorless reaction
  2. customThe solids were triturated with EtOAc
  3. customthen dried at 40° C

Sources & evidence

ORD record
ord-b6078678f4d94971b2271c18244398c2
Source dataset
uspto-grants-2009_05
Patent number
US07528115B2

Reaction notes

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