Benzaldehyde → HCID 178496722, compound

HRID 2087065Notes

Reaction equation

HRID 2087065 reaction equation
N[CH2:2][CH:3]1[O:7][CH:6]([O:8][CH:9]([CH:49]2[CH:53]([OH:54])[CH:52]([OH:55])[CH:51]([N:56]3[CH:61]=[CH:60][C:59](=[O:62])[NH:58][C:57]3=[O:63])[O:50]2)[CH:10]([C:46]([OH:48])=[O:47])[NH:11][CH2:12][CH2:13][CH2:14][NH:15][C:16](=[O:45])[CH:17]([CH:40]([OH:44])[CH:41]([CH3:43])[CH3:42])[NH:18][C:19](=[O:39])[CH:20]([CH:32]2[CH2:37][CH2:36][NH:35][C:34](=[NH:38])[NH:33]2)[NH:21][C:22](=[O:31])[NH:23][CH:24]([CH:28]([CH3:30])[CH3:29])[C:25]([OH:27])=[O:26])[CH:5]([O:64][CH3:65])[CH:4]1[OH:66].[CH:67](=O)[C:68]1[CH:73]=[CH:72][CH:71]=[CH:70][CH:69]=1.[BH3-][C:76]#[N:77].[Na+].Cl>CO>[CH2:67]([N:11]([CH:10]([C@@H:9]([O:8][CH:6]1[C@H:5]([O:64][CH3:65])[C@@H:4]([OH:66])[C@@H:3]([CH2:2][NH:77][CH2:76][C:68]2[CH:73]=[CH:72][CH:71]=[CH:70][CH:69]=2)[O:7]1)[C@@H:49]1[C@@H:53]([OH:54])[C@@H:52]([OH:55])[C@H:51]([N:56]2[CH:61]=[CH:60][C:59](=[O:62])[NH:58][C:57]2=[O:63])[O:50]1)[C:46]([OH:48])=[O:47])[CH2:12][CH2:13][CH2:14][NH:15][C:16](=[O:45])[CH:17]([CH:40]([OH:44])[CH:41]([CH3:43])[CH3:42])[NH:18][C:19](=[O:39])[CH:20]([CH:32]1[CH2:37][CH2:36][NH:35][C:34](=[NH:38])[NH:33]1)[NH:21][C:22](=[O:31])[NH:23][CH:24]([CH:28]([CH3:30])[CH3:29])[C:25]([OH:27])=[O:26])[C:68]1[CH:73]=[CH:72][CH:71]=[CH:70][CH:69]=1

Participants

6

Reactant 4

HCID 240BenzaldehydeHCID 313Hydrochloric AcidHCID 5003444Sodium cyanoborohydrideHCID 17849389816-({[5-(aminomethyl)-4-hydroxy-3-methoxytetrahydro-2-furanyl]oxy}{5-[2,4-dioxo-3,4-dihydro-1 (2H)-pyrimidinyl]-3,4-dihydroxytetrahydro-2-furanyl}methyl)-9-(1-hydroxy-2-methylpropyl)-6-(2-iminohexahydro-4-pyrimidinyl)-2-isopropyl-4,7,10-trioxo-3,5,8,11, 15-pentaazaheptadecane-1,17-dioic acid

Product 1

HCID 178496722HCID 178496722, compoundYield 4.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 50 mg (53 μmol) 16-({[5-(aminomethyl)-4-hydroxy-3-methoxytetrahydro-2-furanyl]oxy}{5-[2,4-dioxo-3,4-dihydro-1 (2H)-pyrimidinyl]-3,4-dihydroxytetrahydro-2-furanyl}methyl)-9-(1-hydroxy-2-methylpropyl)-6-(2-iminohexahydro-4-pyrimidinyl)-2-isopropyl-4,7,10-trioxo-3,5,8,11,15-pentaazaheptadecane-1,17-dioic acid (λmax nm in water=259) in 0.4 ml of methanol is added 11 mg (2.0 eq., 106 μmol) of benzaldehyde and 3.3 mg (1.0 eq., 53 μmol) of NaBH3CN. After stirring for 5 minutes, 0.04 ml of methanolic hydrochloric acid is added. The reaction mixture is then stirred for 0.5 hour. The reaction is monitored by MS. The solvent is removed under reduced pressure to give a yellow gum. The desired products are separated by preparative HPLC to give 15 mg (26% yield) of Example 20a as a white solid and 2.5 mg (4% yield) of Example 20b as a white solid.

Workup

  1. stirringThe reaction mixture is then stirred for 0.5 hour
  2. customThe solvent is removed under reduced pressure
  3. customto give a yellow gum
  4. customThe desired products are separated by preparative HPLC

Sources & evidence

ORD record
ord-62a78eeccb874712aa220a62f5b00ecc
Source dataset
uspto-grants-2004_04
Patent number
US06727232B2

Reaction notes

Loading…