Thiourea → HCID 11167683, compound

HRID 2408223Notes

Reaction equation

HRID 2408223 reaction equation
[C:1]([O:4][C@@H:5]1[C@@H:10]([O:11][C:12](=[O:14])[CH3:13])[C@@H:9]([O:15][C:16](=[O:18])[CH3:17])[C@@H:8]([CH2:19][O:20][C:21](=[O:23])[CH3:22])[O:7][C@@H:6]1Br)(=[O:3])[CH3:2].[NH2:25][C:26]([NH2:28])=[S:27]>CC(C)=O>[C:1]([O:4][C@@H:5]1[C@@H:10]([O:11][C:12](=[O:14])[CH3:13])[C@@H:9]([O:15][C:16](=[O:18])[CH3:17])[C@@H:8]([CH2:19][O:20][C:21](=[O:23])[CH3:22])[O:7][C@H:6]1[S:27][C:26](=[NH:25])[NH2:28])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 2723790ThioureaHCID 2734143alpha-Acetobromogalactose

Product 1

HCID 11167683HCID 11167683, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl bromide (37.5 g) dissolved in acetone (180 ml) with thiourea (10.9 g) at 25° C. Batch heated to reflux for a minimum of 2 hrs. Reaction followed by TLC (1:1 petrol/EtOAc. Starting material 0.69, plus multiple peaks below. Product is a salt and therefore seen on baseline (uv-active)). Batch cooled to R.T. and crystallised as a white crystalline solid (35 g, 79%) with the aid of petrol as anti-solvent. M.p=169-171° C. (Lit3 169° C.). [α]D22+17 (EtOH, C=2.0) (Lit3+16). (1H NMR (DMSO, 400 MHz). δ=1.96, 2.02, 2.09, 2.14 (sx4, 4×3H, —C(O)CH3), 4.08-4.11 (m, 2H, H-6, H-61), 4.4 (t, J6.2 Hz, 1H, H-5), 5.1 (t, J2,39.9 Hz, 1H, H-2), 5.2 (dd, J2,39.9 Hz, J3,43.4 Hz, 1H, H-3), 5.4 (d, J3.3 Hz, 1H, H-4), 5.6 (d, J1,210 Hz, 1H, H-1), 9.2 (Br, 4H, 2×NH2).

Workup

  1. temperatureBatch heated
  2. temperatureto reflux for a minimum of 2 hrs
  3. customReaction
  4. customcrystallised as a white crystalline solid (35 g, 79%) with the aid of petrol as anti-solvent
  5. customM.p=169-171° C. (Lit3 169° C.)

Sources & evidence

ORD record
ord-633d1a18641d42bf878356df29b1a337
Source dataset
uspto-grants-2014_08
Patent number
US08815563B2

Reaction notes

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