Acetic Acid → HCID 10168421, compound

HRID 1061231Notes

Reaction equation

HRID 1061231 reaction equation
C(O)(=O)C.[NH2:5][CH2:6][C@@H:7]([C:9]1[CH:10]=[CH:11][C:12]([OH:20])=[C:13]([NH:15][S:16]([CH3:19])(=[O:18])=[O:17])[CH:14]=1)[OH:8].[O:21]=[C:22]1[N:26]([CH2:27][C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[C:25](=[O:35])[CH:24]([CH2:36][C:37]2[CH:42]=[CH:41][C:40]([N:43]3[CH2:48][CH2:47][C:46](=O)[CH2:45][CH2:44]3)=[CH:39][CH:38]=2)[S:23]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>CN(C=O)C>[C:31]([O:30][C:28](=[O:29])[CH2:27][N:26]1[C:25](=[O:35])[CH:24]([CH2:36][C:37]2[CH:42]=[CH:41][C:40]([N:43]3[CH2:44][CH2:45][CH:46]([NH:5][CH2:6][C@H:7]([OH:8])[C:9]4[CH:10]=[CH:11][C:12]([OH:20])=[C:13]([NH:15][S:16]([CH3:19])(=[O:18])=[O:17])[CH:14]=4)[CH2:47][CH2:48]3)=[CH:39][CH:38]=2)[S:23][C:22]1=[O:21])([CH3:34])([CH3:32])[CH3:33]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 5049666Sodium triacetoxyborohydrideHCID 12047933(R)-N-(5-(2-amino-1-hydroxyethyl)-2-hydroxyphenyl)methanesulfonamideHCID 22220437HCID 22220437, compound

Product 1

HCID 10168421HCID 10168421, compoundYield 68.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Acetic acid (0.12 mL, 2.16 mmol) was added to a mixture of N-{5-[(1R)-2-amino-1-hydroxyethyl]-2-hydroxyphenyl}methanesulfonamide (266 mg, 1.08 mmol) (which was obtained in Example 10), tert-butyl 2-{2,4-dioxo-5-[4-(4-oxo-1-piperidineyl)benzyl]-1,3-thiazolidin-3-yl}acetate (450 mg, 1.08 mmol) (which was obtained in Example 49), and DMF (5 mL). The mixture was stirred for 20 minutes and then, sodium triacetoxyborohydride (276 mg, 1.3 mmol) was added, and the new mixture was stirred at room temperature for 24 hours. The volatiles were removed in vacuo and the residue was purified by flash chromatography (dichloromethane/methyl alcohol 5/1) to produce a yellow solid (480 mg, 68% yield); mp 130-132° C.; 1H NMR (400 MHz, DMSO-d6) δ 1.20-1.50 (m, 11H), 1.81-1.85 (m, 2H), 2.60-2.80 (m, 4H), 2.85-2.9 (m, 4H), 3.40 (m, 1H), 3.60 (m, 1H), 4.20 (s, 2H), 4.50 (m, 1H), 5.04 (m, 1H), 6.80-6.87 (m, 3H), 7.02 (m, 1H), 7.08 (m, 2H), 7.20 (m, 1H); Anal. Calcd. for C30H40N4O8S2: C, 55.54; H, 6.21; N, 8.64. Found: C, 53.86; H, 6.11; N, 7.65.

Workup

  1. stirringthe new mixture was stirred at room temperature for 24 hours
  2. customThe volatiles were removed in vacuo
  3. customthe residue was purified by flash chromatography (dichloromethane/methyl alcohol 5/1)

Sources & evidence

ORD record
ord-50adf7a8d40f447a87537eaae4e781e6
Source dataset
uspto-grants-2003_02
Patent number
US06525202B2

Reaction notes

Loading…