Ammonium formate → HCID 86751596, compound

HRID 2293792Notes

Reaction equation

HRID 2293792 reaction equation
C([O:8][C:9]([C@H:11]([C:13]1[CH:14]=[C:15]([NH:19][C:20](=[O:46])[NH:21][CH2:22][C:23]([N:25]2[C@@H:29]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[C@H:28]([C:36]([OH:38])=[O:37])[S:27][C@H:26]2[C:39]([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40])=[O:24])[CH:16]=[CH:17][CH:18]=1)[CH3:12])=[O:10])C1C=CC=CC=1.C([O-])=O.[NH4+]>[Pd].CO>[C:42]([O:41][C:39]([C@H:26]1[N:25]([C:23](=[O:24])[CH2:22][NH:21][C:20](=[O:46])[NH:19][C:15]2[CH:14]=[C:13]([CH:11]([CH3:12])[C:9]([OH:10])=[O:8])[CH:18]=[CH:17][CH:16]=2)[C@@H:29]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[C@H:28]([C:36]([OH:38])=[O:37])[S:27]1)=[O:40])([CH3:43])([CH3:44])[CH3:45]

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 86751594HCID 86751594, compound

Product 1

HCID 86751596HCID 86751596, compoundYield 42.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

The process is performed as in Example 4, but starting with 0.58 g of (2S,4S,5R)-3-{2-{3-[(S)-3-(1-benzyloxycarbonylethyl)phenyl]ureido}acetyl}-2-tert-butoxycarbonyl-4-phenyl-5-thiazolidinecarboxylic acid, 0.34 g of ammonium formate and 0.6 g of 10% palladium-on-charcoal. 0.21 g of 2-{3-{3-[2-((2S,4S,5R)-2-tert-butoxycarbonyl-5-carboxy-4-phenyl-3-thiazolidinyl)-2-oxoethyl]ureido}phenyl}propionic acid is thus obtained in the form of a white solid melting at 142° C., [α]D25 =+24.5°±0.6° (c=1.01; MeOH); 1H NMR (200 MHz, (CD3)2SO with addition of a few drops of CD3COOD, at a temperature of 373 K, δ in ppm): 1.41 (d, J=7 Hz, 3H: CH3); 1.51 (s, 9H: CH3 of the tert-butyl); 3.62 (q, J=7 Hz, 1H: CHCOO); 3.66 and 4.05 (broad d and d respectively, J=17.5 Hz, 1H each: COCH2 N); 4.18 (d, J=4 Hz, 1H: H at C5 of the ring); 5.72 (s, 1H: H at C2 of the ring); 5.77 (d, J=4 Hz, 1H: H at C4 of the ring); 6.86 (broad d, J=7.5 Hz, 1H: aromatic H (H ortho to the CH)); 7.17 (t, J=7.5 Hz, 1H: aromatic H (H meta to the CH); from 7.20 to 7.50 (mt, 5H: aromatic H); 7.73 (dd, J=7.5 and 1.5 Hz, 2H: H ortho to the phenyl).

Sources & evidence

ORD record
ord-ad3dfc1978014f8383aa73e990c801a3
Source dataset
uspto-grants-1997_11
Patent number
US05686622

Reaction notes

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