Acetic Acid → HCID 68862840, compound

HRID 1725969Notes

Reaction equation

HRID 1725969 reaction equation
[NH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][C@H:2]1[CH2:7][CH2:8][NH:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[S:16]([NH:19][C:20]1[CH:29]=[CH:28][C:27]2[CH2:26][CH2:25][CH2:24][CH2:23][C:22]=2[C:21]=1[C:30]([OH:32])=[O:31])(=[O:18])=[O:17].C(O)(=O)C.[C:37]1(=O)[CH2:41][CH2:40][CH2:39][CH2:38]1.C([BH3-])#N>CN(C=O)C>[CH:37]1([N:1]2[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]2[CH2:7][CH2:8][NH:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[S:16]([NH:19][C:20]2[CH:29]=[CH:28][C:27]3[CH2:26][CH2:25][CH2:24][CH2:23][C:22]=3[C:21]=2[C:30]([OH:32])=[O:31])(=[O:18])=[O:17])[CH2:41][CH2:40][CH2:39][CH2:38]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 8452CyclopentanoneHCID 498716Cyano-borohydrideHCID 68866187HCID 68866187, compound

Product 1

HCID 68862840HCID 68862840, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

A solution of Example 401A (0.022 g, 0.044 mmol) in DMF (1.0 mL) was treated with acetic acid (0.05 mL) and cyclopentanone (0.005 mL, 0.06 mmol). The mixture was shaken at 50° C. for 20 minutes, treated with macroporous polystyrene bound cyanoborohydride resin (47 mg, 0.13 mmol), shaken at 70° C. for 15 hours, concentrated, and purified by C18 reverse-phase HPLC using acetonitrile/water/0.1% TFA to provide the desired product. MS (DCI) m/e 526 (M+H)+; 1H NMR (500 MHz, DMSO-d6) δ 13.21 (br s, 1H), 7.54 (d, 1H), 7.40 (t, 1H), 6.93 (br s, 1H), 6.84 (d, 1H), 6.65 (t, 2H), 6.03 (br s, 1H), 4.02 (br s, 1H), 3.63 (br s, 1H), 3.35 (br s, 3H), 2.99 (br s, 1H), 2.70 (br s, 2H), 2.63 (br s, 2H), 2.00 (br s, 4H), 1.83 (br s, 3H), 1.65-1.54 (m, 13H).

Workup

  1. stirringshaken at 70° C. for 15 hours
  2. concentrationconcentrated
  3. custompurified by C18 reverse-phase

Sources & evidence

ORD record
ord-8ce39cb56d824645bc358ba4344e1f95
Source dataset
uspto-grants-2009_02
Patent number
US07491718B2

Reaction notes

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