Acetic Acid → HCID 69746391, compound

HRID 1814422Notes

Reaction equation

HRID 1814422 reaction equation
[CH:1]1[C:13]2[CH:12]([CH2:14][O:15][C:16]([NH:18][C@@H:19]([CH2:27][CH2:28][NH:29][CH:30]3[C:39]4[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=4)[CH2:33][CH2:32][CH2:31]3)[C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])=[O:17])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.[CH2:40]([CH:45]=O)[CH2:41][C:42]([OH:44])=[O:43].CC(O)=O.[BH3-]C#N.[Na+]>CO.O>[C:23]([O:22][C:20]([C@@H:19]([NH:18][C:16]([O:15][CH2:14][CH:12]1[C:11]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=2[C:5]2[C:13]1=[CH:1][CH:2]=[CH:3][CH:4]=2)=[O:17])[CH2:27][CH2:28][N:29]([CH:30]1[C:39]2[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=2)[CH2:33][CH2:32][CH2:31]1)[CH2:45][CH2:40][CH2:41][C:42]([OH:44])=[O:43])=[O:21])([CH3:26])([CH3:24])[CH3:25]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 11124-Oxobutanoic acidHCID 5003444Sodium cyanoborohydrideHCID 91072227HCID 91072227, compound

Product 1

HCID 69746391HCID 69746391, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of tert-butyl (2S)-2-[[(9H-9-fluorenylmethoxy)carbonyl]amino]-4-(1,2,3,4-tetrahydro-1-naphthylamino)butanoate (16 mg,0.030 mmol) in MeOH (0.5 ml) were added succinic semialdehyde (15 wt. % solution in water, 48 μl, 0.077 mmol), HOAc (2 μl, 0.035 mmol) and NaBH3CN (2.3 mg, 0.074 mmol), and the mixture was stirred at RT for 6 h. After adding water, the mixture was extracted with chloroform, washed with brine, dried over magnesium sulfate, and filtered. The filtrate was concentrated under vacuum to dryness, and the residue was adsorbed on a plate of silica gel and then developed with 10% methanol/chloroform to afford 4-[[(3S)-3-(tert-butoxycarbonyl)-3-[[(9H-9-fluorenylmethoxy)carbonyl]amino]propyl](1,2,3,4-tetrahydro-1-naphthyl)amino]butanoic acid (18 mg, 98%): MS(ES+) m/e 613 [M+H]+; 1H NMR (400 MHz, CDCl3) δ 7.98 (br, 1H), 7.76 (d, J=7.3 Hz, 2H), 7.61 (m, 3H), 7.40 (t, J=7.3 Hz, 2H), 7.31 (m, 2H), 7.15 (m, 2H), 7.06 (d, J7.6 =Hz, 1H), 5.64 (br, 1H), 4.36 (m, 2H), 4.22 (m, 3H), 2.75-2.17 (m, 8H), 2.10-1.65 (m, 8H), 1.42 (s, 9H).

Workup

  1. extractionthe mixture was extracted with chloroform
  2. washwashed with brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated under vacuum to dryness

Sources & evidence

ORD record
ord-10e6cba27773492ba2a135c2805e201e
Source dataset
uspto-grants-2005_04
Patent number
US06875884B1

Reaction notes

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