Hydrochloric Acid → HCID 66879498, compound

HRID 1015521Notes

Reaction equation

HRID 1015521 reaction equation
[NH2:1][C:2]([C@@H:4]1[CH2:8][S:7][CH2:6][N:5]1C(OC(C)(C)C)=O)=[O:3].[ClH:16]>C(OC(=O)C)C>[ClH:16].[S:7]1[CH2:8][C@@H:4]([C:2]([NH2:1])=[O:3])[NH:5][CH2:6]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 51340398HCID 51340398, compound

Product 1

HCID 66879498HCID 66879498, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

To a stirred solution of tert-butyl (4R)-4-(aminocarbonyl)-1,3-thiazolidine-3-carboxylate (23 g, 0.1 mol) in ethylacetate (50 mL) at 0° C. was added dry HCl in ethylacetate (3.5 N, 250 mL). The resulting mixture was stirred at room temperature for 2 h, the volatiles were removed under reduced pressure and the residue was triturated with ethylacetate several times to obtain (4R)-1,3-thiazolidine-4-carboxamide hydrochloride salt as an off-white powder (16.5 g) quantitatively. M.R, 201.8-203.9° C.; m/z (M+1), 133; IR cm−1 3387, 3250, 3189, 2857, 1706, 1675, 1612, 1371, 1123, 894; 1H NMR (DMSO-d6) 300 MHz δ 10.30-9.60 (s (br), ½H), 8.10 (s (br), ½H), 7.77 (s (br), 1H), 4.40 (t, J=7.0 Hz, 1H), 4.31 (d, J=9.6 Hz, 1H), 4.25 (d, J=9.6 Hz, 1H), 3.50-3.30 (m, 1H), 3.15 (dd, J=7.0, 11.7 Hz, 1H).

Workup

  1. customthe volatiles were removed under reduced pressure
  2. customthe residue was triturated with ethylacetate several times

Sources & evidence

ORD record
ord-fb1611306b524d58b7731c5fffcc583b
Source dataset
uspto-grants-2011_07
Patent number
US07985759B2

Reaction notes

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