(5R,9R)-tert-butyl 9-(dodecyloxy)-1-(9H-fluoren-9-yl)-3-oxo-2,11-dioxa-7-thia-4-azatricosane-5-carboxylate → (R)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-(((R)-2,3-bis(dodecyloxy)propyl)thio)propanoic acid

HRID 2205020Notes

Reaction equation

HRID 2205020 reaction equation
[CH2:1]([O:13][C@H:14]([CH2:44][O:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH3:57])[CH2:15][S:16][CH2:17][C@@H:18]([C:37]([O:39]C(C)(C)C)=[O:38])[NH:19][C:20](=[O:36])[O:21][CH2:22][CH:23]1[C:35]2[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=2[C:29]2[C:24]1=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]>C(O)(C(F)(F)F)=O.C(Cl)Cl.CC(OC)(C)C>[CH:34]1[C:35]2[CH:23]([CH2:22][O:21][C:20]([NH:19][C@@H:18]([CH2:17][S:16][CH2:15][C@H:14]([O:13][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])[CH2:44][O:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH3:57])[C:37]([OH:39])=[O:38])=[O:36])[C:24]3[C:29](=[CH:28][CH:27]=[CH:26][CH:25]=3)[C:30]=2[CH:31]=[CH:32][CH:33]=1

Participants

5

Reactant 1

HCID 71294734(5R,9R)-tert-butyl 9-(dodecyloxy)-1-(9H-fluoren-9-yl)-3-oxo-2,11-dioxa-7-thia-4-azatricosane-5-carboxylate

Product 1

HCID 67400890(R)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-(((R)-2,3-bis(dodecyloxy)propyl)thio)propanoic acid

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolventHCID 15413tert-Butyl methyl etherSolvent

Procedure

A solution of (5R,9R)-tert-butyl 9-(dodecyloxy)-1-(9H-fluoren-9-yl)-3-oxo-2,11-dioxa-7-thia-4-azatricosane-5-carboxylate in 50% TFA in DCM (0.3 M) was stirred at room temperature until complete deprotection of tert-butyl group (30 minutes). The reaction mixture was diluted in MTBE, washed three times with 1M citric acid (adjusted to pH3), and once with 1:2 1N HCl/brine. The organic layer was dried over anhydrous Na2SO4 and concentrated en vaccuo. The resulting waxy solid was used for the next step without further purification.

Workup

  1. washwashed three times with 1M citric acid (adjusted to pH3)
  2. dry with materialThe organic layer was dried over anhydrous Na2SO4
  3. concentrationconcentrated en vaccuo
  4. customThe resulting waxy solid was used for the next step without further purification

Sources & evidence

ORD record
ord-1611701be15d4d59a813a5e33c23ebdd
Source dataset
uspto-grants-2016_06
Patent number
US09365506B2

Reaction notes

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