Butylamine → HCID 131720006, compound

HRID 1779841Notes

Reaction equation

HRID 1779841 reaction equation
[CH2:1]([NH:5][C:6](=[O:39])[C@H:7]([CH:36]([CH3:38])[CH3:37])[CH2:8][C@H:9]([OH:35])[C@@H:10]([N:32]=[N+]=[N-])[CH2:11][C@@H:12]([CH:29]([CH3:31])[CH3:30])[CH:13]([OH:28])[C:14]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[C:16]([CH2:22][CH:23](OC)[O:24][CH3:25])[CH:15]=1)[CH2:2][CH2:3][CH3:4].C([C@H]1[C@@H]([C@@H](N=[N+]=[N-])C[C@@H](C(C)C)C(O)C2C=CC(OC)=C(CCOCOC)C=2)C[O:45][C:44]1=O)(C)C.C(N)CCC>>[CH2:1]([NH:5][C:6](=[O:39])[C@H:7]([CH:36]([CH3:38])[CH3:37])[CH2:8][C@H:9]([OH:35])[C@@H:10]([NH2:32])[CH2:11][C@@H:12]([CH:29]([CH3:30])[CH3:31])[CH:13]([OH:28])[C:14]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[C:16]([CH2:22][CH2:23][O:24][CH2:25][O:45][CH3:44])[CH:15]=1)[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 3

HCID 8007ButylamineHCID 131720008HCID 131720008, compoundHCID 131720009HCID 131720009, compound

Product 1

HCID 131720006HCID 131720006, compound

Procedure

5(S)-Azido-4(S),8(R,S)-dihydroxy-2(S),7(S)-diisopropyl-8-[4-methoxy-3-(2-methoxy-methoxyethyl)-phenyl]-octanoic acid (N-butyl)-amide A solution of 400 mg of 3(S)-isopropyl-4(S)-{1(S)-azido-4(R,S)-hydroxy-3(S)-isopropyl -4-[4-methoxy-3-(2-methoxymethoxyethyl)-phenyl]-butyl}-tetrahydrofuran-2-one (Example 81d) and 3.8 ml of n-butylamine is stirred for 16 hours at 50° C. and then concentrated by evaporation. Purification of the residue by FC (50 g of silica gel, hexane/ethyl acetate=1:1) yields the title compound: Rf (hexane/ethyl acetate=1:1)=0.44; HPLC Rt =16.13 and 17.03 minutes (diastereoisomeric mixture).

Workup

  1. concentrationconcentrated by evaporation
  2. customPurification of the residue by FC (50 g of silica gel, hexane/ethyl acetate=1:1)

Sources & evidence

ORD record
ord-bbf83aa2c4e54c01b87f1bcc98b996ec
Source dataset
uspto-grants-1997_05
Patent number
US05627182

Reaction notes

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