Isopropyl chloroformate → HCID 67018565, compound

HRID 490050Notes

Reaction equation

HRID 490050 reaction equation
[C:1]([Si:5]1([C:30]([CH3:33])([CH3:32])[CH3:31])[O:10][CH:9]2[CH:11]([OH:29])[CH:12]([N:14]3[C:18]4[N:19]=[C:20]([N:23]=[CH:24][N:25]([CH3:27])[CH3:26])[N:21]=[CH:22][C:17]=4[S:16][C:15]3=[O:28])[O:13][CH:8]2[CH2:7][O:6]1)([CH3:4])([CH3:3])[CH3:2].Cl[C:35]([O:37][CH:38]([CH3:40])[CH3:39])=[O:36]>C(Cl)Cl.CN(C1C=CN=CC=1)C>[CH:38]([O:37][C:35](=[O:36])[O:29][CH:11]1[CH:9]2[O:10][Si:5]([C:1]([CH3:4])([CH3:3])[CH3:2])([C:30]([CH3:33])([CH3:32])[CH3:31])[O:6][CH2:7][CH:8]2[O:13][CH:12]1[N:14]1[C:18]2[N:19]=[C:20]([N:23]=[CH:24][N:25]([CH3:27])[CH3:26])[N:21]=[CH:22][C:17]=2[S:16][C:15]1=[O:28])([CH3:40])[CH3:39]

Participants

5

Reactant 2

HCID 7917Isopropyl chloroformateHCID 67018545HCID 67018545, compound

Product 1

HCID 67018565HCID 67018565, compoundYield 51%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

N′-[3-(2,2-Di-tert-butyl-7-hydroxy-tetrahydro-furo[3,2-d][1,3,2]dioxasilin-6-yl)-2-oxo-2,3-dihydro-thiazolo[4,5-d]pyrimidin-5-yl]-N,N-dimethyl-formamidine (1.83 g, 3.68 mmol) was dissolved in DCM (18.4 mL) and DMAP (450 mg, 3.68 mmol) was added. Isopropyl chloroformate (7.37 mL, 1 M in toluene, 7.37 mmol) was added over 12 h via syringe pump. The reaction was stirred an additional 5 h following addition then concentrated in vacuo. The residue was submitted to flash chromatography (50-100% EtOAc-Hex) yielding 1.09 g (51%) of 14 as a white solid: 1H NMR (400 MHz, DMSO-d6) δ 8.61 (1H, s), 8.60 (1H, s), 6.27 (1H, t, J=7.4 Hz), 6.10 (1H, d, J=7.9 Hz), 5.06 (1H, t, J=6.9 Hz), 4.61 (1H, septet, J=6.1 Hz), 4.49 (1H, t, J=10.5 Hz), 4.30-4.36 (1H, m), 3.93 (1H, dd, J1=5.3 Hz, J2=10.8 Hz), 3.14 (3H, s), 3.03 (3H, s), 1.14 (3H, d, J=6.2 Hz), 1.04 (3H, d, J=5.4 Hz), 1.04 (3H, s), 1.00-1.03 (18H, m)8.61 (1H, s), 8.60 (1H, s), 6.27 (1H, t, J=7.4 Hz), 6.10 (1H, d, J=7.9 Hz), 5.06 (1H, t, J=6.9 Hz), 4.61 (1H, septet, J=6.1 Hz), 4.49 (1H, t, J=10.5 Hz), 4.30-4.36 (1H, m), 3.93 (1H, dd, J1=5.3 Hz, J2=10.8 Hz), 3.14 (3H, s), 3.03 (3H, s), 1.14 (3H, d, J=6.2 Hz), 1.04 (3H, d, J=5.4 Hz), 1.04 (3H, s), 1.00-1.03 (18H, m). [M+H]+ @ m/z 583.0.

Workup

  1. additionaddition
  2. concentrationthen concentrated in vacuo

Sources & evidence

ORD record
ord-3906d17318f4478889d722fcb761f3a8
Source dataset
uspto-grants-2009_05
Patent number
US07528115B2

Reaction notes

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