Methanol → HCID 13934659, compound

HRID 652084Notes

Reaction equation

HRID 652084 reaction equation
[C:1]([O:9][CH:10]([P:12]([O:48]C)([O:14][C@@H:15]([CH2:33][CH2:34][CH2:35][CH2:36][NH:37][C:38]([O:40][CH2:41][C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1)=[O:39])[C:16]([N:18]1[CH2:32][CH2:31][CH2:30][C@H:19]1[C:20]([O:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=[O:21])=[O:17])=[O:13])[CH3:11])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CN(C)C.C(OC(P(O)(OC(NC(OCC1C=CC=CC=1)=O)CCCCC([C@]1(C(OCC2C=CC=CC=2)=O)CCCN1)=O)=O)C)(=O)C1C=CC=CC=1.CO>CC(C)=O.C(Cl)Cl.C(O)(=O)C>[C:1]([O:9][CH:10]([P:12]([OH:48])([O:14][C@@H:15]([CH2:33][CH2:34][CH2:35][CH2:36][NH:37][C:38]([O:40][CH2:41][C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1)=[O:39])[C:16]([N:18]1[CH2:32][CH2:31][CH2:30][C@H:19]1[C:20]([O:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=[O:21])=[O:17])=[O:13])[CH3:11])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

8

Reactant 4

HCID 887MethanolHCID 1146TrimethylamineHCID 131715173HCID 131715173, compoundHCID 131715174HCID 131715174, compound

Product 1

HCID 13934659HCID 13934659, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 180AcetoneSolventHCID 6344DichloromethaneSolvent

Procedure

The phenylmethyl ester product from part (c) (1.0 g.) in acetone (10 ml.) is saturated with trimethylamine and heated in a sealed tube at 75°-80° for 16 hours. The reaction mixture is evaporated and the residue is dissolved in ethyl acetate, washed with 1N hydrochloric acid and brine, dried over sodium sulfate, and concentrated in vacuo to yield 0.82 g. of 1-[(S)-2-[[[1-(benzoyloxy)ethyl]hydroxyphosphinyl]oxy-1-oxo-6-[[(phenylmethoxy)carbonyl]amino]hexyl]-L-proline, phenylmethyl ester. TLC (silica gel; methanol:acetic acid:methylene chloride, 1:1:20) Rf =0.21.

Workup

  1. temperatureheated in a sealed tube at 75°-80° for 16 hours
  2. customThe reaction mixture is evaporated
  3. dissolutionthe residue is dissolved in ethyl acetate
  4. washwashed with 1N hydrochloric acid and brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customto yield 0.82 g

Sources & evidence

ORD record
ord-d7b73819314749159c0063caf1be7170
Source dataset
uspto-grants-1987_06
Patent number
US04670422

Reaction notes

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