Hydrochloric Acid → HCID 67086980, compound

HRID 2365538Notes

Reaction equation

HRID 2365538 reaction equation
C(OC(=O)[NH:7][CH2:8][C@H:9]([NH:25]C(OC(C)(C)C)=O)[CH2:10][CH2:11][CH2:12][C:13]1[CH:18]=[CH:17][C:16]([O:19][CH2:20][C@H:21]([OH:24])[CH2:22][OH:23])=[CH:15][CH:14]=1)(C)(C)C.Cl>CCOCC>[NH2:25][C@@H:9]([CH2:8][NH2:7])[CH2:10][CH2:11][CH2:12][C:13]1[CH:18]=[CH:17][C:16]([O:19][CH2:20][C@H:21]([OH:24])[CH2:22][OH:23])=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 67120713HCID 67120713, compound

Product 1

HCID 67086980HCID 67086980, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

{(R)-2-tert-Butoxycarbonylamino-5-[4-((R)-2,3-dihydroxy-propoxy)-phenyl]-pentyl}-carbamic acid tert-butyl ester (94 mg, 0.201 mmol) is stirred with a solution of 1 M HCl in Et2O (3 ml) for 18 hours and then loaded onto a 1 g SCX-2 cartridge washed with MeOH (30 ml), followed by 7M NH3 in MeOH (30 ml). The NH3 fraction is concentrated in vacuo to give the title compound, (R)-3-[4-((R)-4,5-Diamino-pentyl)-phenoxy]-propane-1,2-diol Intermediate H (R)-3-[4-((R)-4,5-Diamino-pentyl)-phenoxy]-propane-1,2-diol; [M+H]+ 269

Workup

  1. washwashed with MeOH (30 ml)
  2. concentrationThe NH3 fraction is concentrated in vacuo

Sources & evidence

ORD record
ord-929186a35e2043fcb2fed282d66a01b3
Source dataset
uspto-grants-2014_04
Patent number
US08697687B2

Reaction notes

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