Acetic Acid → HCID 57684697, compound

HRID 1175235Notes

Reaction equation

HRID 1175235 reaction equation
[C:1](O)(=[O:3])[CH3:2].CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.[Cl:26][C:27]1[CH:44]=[CH:43][C:42]([C@H:45]2[C@H:50]([O:51][CH2:52][C:53]3[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=3)[C@@H:49]([O:59][CH2:60][C:61]3[CH:66]=[CH:65][CH:64]=[CH:63][CH:62]=3)[C@H:48]([O:67][CH2:68][C:69]3[CH:74]=[CH:73][CH:72]=[CH:71][CH:70]=3)[C@@H:47]([CH2:75][O:76][CH2:77][C:78]3[CH:83]=[CH:82][CH:81]=[CH:80][CH:79]=3)[O:46]2)=[CH:41][C:28]=1[CH2:29][C:30]1[CH:40]=[CH:39][C:33]([CH2:34][NH:35][CH:36]2[CH2:38][CH2:37]2)=[CH:32][CH:31]=1>C(Cl)Cl.CCN(CC)CC>[Cl:26][C:27]1[CH:44]=[CH:43][C:42]([C@H:45]2[C@H:50]([O:51][CH2:52][C:53]3[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=3)[C@@H:49]([O:59][CH2:60][C:61]3[CH:62]=[CH:63][CH:64]=[CH:65][CH:66]=3)[C@H:48]([O:67][CH2:68][C:69]3[CH:70]=[CH:71][CH:72]=[CH:73][CH:74]=3)[C@@H:47]([CH2:75][O:76][CH2:77][C:78]3[CH:79]=[CH:80][CH:81]=[CH:82][CH:83]=3)[O:46]2)=[CH:41][C:28]=1[CH2:29][C:30]1[CH:40]=[CH:39][C:33]([CH2:34][N:35]([CH:36]2[CH2:37][CH2:38]2)[C:1](=[O:3])[CH3:2])=[CH:32][CH:31]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 57684686HCID 57684686, compound

Product 1

HCID 57684697HCID 57684697, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8471TriethylamineSolvent

Procedure

To a solution of acetic acid (0.11 g) and Et3N (0.14 mL) in CH2Cl2 (1 mL) at room temperature, EDCI (96 mg) and HOBt (68 mg) was added. The mixture was stirred for 30 min at room temperature. A solution of N-(4-(2-chloro-5-((2S,3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)tetrahydro-2H-pyran-2-yl)benzyl)benzyl)cyclopropanamine (Intermediate AQ) (40 mg) in CH2Cl2 (0.2 mL) was added dropwise. The reaction was monitored by LC-MS. After the starting material was consumed, CH2Cl2 was added to dilute the solution. The resulting mixture was then washed with H2O, 1N HCl, aqueous NaHCO3 and brine. CH2Cl2 was removed under reduced pressure, and the crude product was purified by preparative TLC to give intermediate AR (20 mg). MS ESI (m/z): 836 (M+H)+, 853 (M+NH4)+.

Workup

  1. customAfter the starting material was consumed
  2. additionCH2Cl2 was added
  3. additionto dilute the solution
  4. washThe resulting mixture was then washed with H2O, 1N HCl, aqueous NaHCO3 and brine
  5. customCH2Cl2 was removed under reduced pressure
  6. customthe crude product was purified by preparative TLC
  7. customto give intermediate AR (20 mg)

Sources & evidence

ORD record
ord-718059be3a7b44cbb0122309e5f10516
Source dataset
uspto-grants-2010_11
Patent number
US07838499B2

Reaction notes

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